26 Flared Leggings Outfits & Trends & How to Style Flare Leggings in 2026

Last Updated: February 03, 2026

Okay, so you've got those flared leggings and you're wondering how to make them look amazing, right? Like, beyond just throwing on a hoodie? Totally get it!

They're back in a big way, and trust me, you can totally rock them for so many occasions. We're talking comfy-chic that actually looks put-together.

I’m going to show you all the best ways to style them so you’ll feel confident and super on-trend, whether you’re grabbing coffee, heading to a casual brunch, or even dressing them up a little for a night out.

You're going to love how versatile they are once you see these outfit ideas, get ready to fall in love with your flared leggings all over again!

26 Best Flared Leggings Outfit Ideas

1. Cream Ribbed Tank Top + Beige Ribbed Flare Leggings + Cream Borg Jacket

Cream Ribbed Tank Top + Beige Ribbed Flare Leggings + Cream Borg Jacket
Cream Ribbed Tank Top + Beige Ribbed Flare Leggings + Cream Borg Jacket

Honestly, this outfit just screams effortless chic and cozy vibes all rolled into one! It’s the kind of look that makes you feel put-together without even trying, perfect for those days when you want to be comfortable but still look seriously stylish. I love how it balances a relaxed feel with a touch of polish.

The Outfit: I like to start with these super comfy beige ribbed flare leggings. They’re so flattering and have that perfect relaxed feel.

On top, I’ve paired a simple cream ribbed tank top. It’s a classic for a reason! And to really bring the cozy factor up a notch, I’ve layered on this cream borg jacket. It adds amazing texture and warmth, making the whole look feel super inviting and chic.

Accessories you can pair: To finish this off, I'd personally add a delicate gold necklace, something subtle that just peeks out. A small crossbody bag in a neutral tone like taupe or a soft brown would be perfect, keeping the look streamlined.

And for shoes, you could totally rock the cream clogs with socks shown, or even some stylish white sneakers for a more casual vibe.

Why this works? This combo is a winner because of the harmonious color palette and the mix of textures. The ribbed knit of the leggings and tank create a cohesive base, while the fluffy borg jacket adds a playful, luxurious contrast. It’s all about comfort meeting style in the most elegant way possible.

Best for: I see this outfit being perfect for a relaxed weekend brunch, running errands on a chilly day, or even a casual coffee date. It’s your go-to for looking cute and feeling snug when you’re out and about!

2. Navy Jersey Polo + Navy Flared Leggings + White Canvas Sneakers

Navy Jersey Polo + Navy Flared Leggings + White Canvas Sneakers
Navy Jersey Polo + Navy Flared Leggings + White Canvas Sneakers

Honestly, this outfit just screams effortless cool! It’s got this relaxed, sporty vibe but is still super put-together, perfect for when you want to look stylish without trying too hard. You know that feeling when comfort and chic totally collide? That’s this look. It’s playful yet sophisticated, giving off major weekend getaway vibes.

The Outfit: I'm obsessed with how the classic navy and white striped jersey polo just pops against the solid navy flared leggings. The polo has that sporty, collared look that instantly elevates the whole outfit, and the fabric feels so comfy.

Then you’ve got these amazing flared leggings in a deep navy jersey. They’re literally the definition of flared leggings, giving you that flattering silhouette that flows so well.

To finish it off, I love a clean pair of white canvas sneakers. They keep the look grounded and add that perfect sporty touch.

Accessories you can pair: To keep with the sporty and chic vibe, I’d totally add a simple silver pendant necklace. A navy or white baseball cap would be super cute too, especially if you’re out and about. For a bag, a chic canvas tote or a sleek crossbody would work wonders.

Why this works? This combo is a winner because of the perfect balance between sporty elements and a refined silhouette. The stripes on the polo add a fun visual interest, while the solid flares keep it sleek. It’s a timeless color combination, and the flared leggings are just so on-trend and flattering. It’s basically a no-fail recipe for looking effortlessly stylish.

Best for: This is your go-to for a stylish day trip, running errands in style, or even a casual brunch with friends. I can totally picture wearing this on a boardwalk or while exploring a cute seaside town. It's all about relaxed confidence and looking great while doing it.

3. Black Crepe Blazer + Black Ribbed Tank Top + Black Flared Leggings + Black Leather Pointed Heels

Black Crepe Blazer + Black Ribbed Tank Top + Black Flared Leggings + Black Leather Pointed Heels
Black Crepe Blazer + Black Ribbed Tank Top + Black Flared Leggings + Black Leather Pointed Heels

Okay, you know that feeling when an outfit just clicks? Like it’s chic, powerful, and super comfortable all at once? That’s exactly the vibe I’m getting from this look. It’s effortlessly sophisticated with a modern edge, perfect for when you want to feel put-together without trying too hard. Honestly, it’s the kind of outfit that makes you stand a little taller.

The Outfit: I love starting with these Black Flared Leggings because they're seriously a game-changer. They give you that sleek, elongated silhouette that’s so flattering.

Then, I’d pair them with a simple Black Ribbed Tank Top for a clean base. Now, for the magic: a sharp Black Crepe Blazer. It instantly elevates everything, adding that polished touch. I like to make sure the blazer fits just right, nipping in at the waist to highlight your shape.

Accessories you can pair: To really nail this, I'd add a sleek Black Leather Belt to define your waist over the leggings and tank, plus some delicate silver or gold jewelry, maybe a simple necklace or some classic stud earrings.

And of course, you need those Black Leather Pointed Heels! They complete the long, lean line and add that final dose of power.

Why this works? This combination is a total winner because it plays with proportions and textures. The fitted top and blazer contrast beautifully with the dramatic flare of the leggings, creating a balanced and dynamic silhouette. It’s a classic monochrome look that’s timeless, but the flared leg and sharp blazer give it a contemporary, boss-babe feel. It just screams confidence!

Best for: I think this is literally perfect for so many occasions! Think about heading to an important work meeting, going out for a chic dinner date, or even just elevating your everyday style for brunch. It’s versatile enough to take you from day to night with just a quick accessory change.

4. Navy Fleece Pullover + Navy Flared Leggings + White Sneakers

Navy Fleece Pullover + Navy Flared Leggings + White Sneakers
Navy Fleece Pullover + Navy Flared Leggings + White Sneakers

Honestly, this combo is giving me major cool, casual vibes. It's that perfect blend of comfort and style, you know? Like you just threw it on, but you still look totally put-together. It’s effortless chic at its finest, and I’m obsessed with how sleek and modern it feels. It’s the kind of look that makes you feel confident and ready for anything.

The Outfit: I love starting with these super comfy navy flared leggings. They're amazing because they hug you in all the right places but still give you that flowy, relaxed feel at the bottom.

Then, to top it off, I paired them with this cozy navy fleece pullover. It’s got that cool quarter-zip detail, and because it’s slightly cropped, it perfectly complements the high-waisted leggings. It’s the ideal balance of snug and chic.

Accessories you can pair: To keep the look clean and fresh, I’d totally go for some simple white sneakers like the ones shown. You could also add a simple silver pendant necklace or some small hoop earrings for a little sparkle.

A crossbody bag in a neutral tone would be super practical and stylish too.

Why this works? This outfit is a masterclass in monochromatic magic! The consistent navy color throughout makes the silhouette really sleek and elongating. Plus, mixing textures like the smooth leggings with the plush fleece adds that extra bit of interest without being overwhelming. It’s proof that comfort doesn't have to sacrifice style.

Best for: This is your go-to for running errands, grabbing a casual brunch with friends, or even for a relaxed travel day. I can totally see myself wearing this while exploring a new city or just chilling on a cozy weekend. It’s versatile, comfy, and always looks good.

5. White Ribbed Turtleneck + Black Flared Leggings + Charcoal Wool Coat + Black Leather Ankle Boots

White Ribbed Turtleneck + Black Flared Leggings + Charcoal Wool Coat + Black Leather Ankle Boots
White Ribbed Turtleneck + Black Flared Leggings + Charcoal Wool Coat + Black Leather Ankle Boots

Okay, you know that feeling when you want to look put-together but also super comfy? This outfit is totally that vibe! It’s effortlessly chic, a little bit sophisticated, and just perfect for when you need to dash out the door but still want to feel amazing. Honestly, it’s one of those looks that just works, no matter what your day throws at you.

So, let’s break it down. I like to start with a classic white ribbed turtleneck. It’s a great base layer, super soft, and adds a touch of warmth.

Then, we’re pairing it with black flared leggings. These aren't your gym leggings, mind you. They have a more structured feel and that flattering flare that just elongates the legs. I love how they transition from fitted to a gentle flare.

To top it all off, I’ve added a charcoal wool coat. It’s a bit longer, hitting around the knee, and gives the whole outfit a polished, almost tailored feel.

And for shoes? You can’t go wrong with black leather ankle boots with a block heel. They add just the right amount of lift and keep the silhouette sleek.

This combo just works because it plays with proportions and textures. The fitted turtleneck and leggings are balanced by the slightly oversized, structured coat. The monochromatic base of black and white is timeless, and the charcoal coat adds depth without being overwhelming. It’s chic, cozy, and incredibly flattering!

I'd totally rock this for running errands, a casual lunch date, or even a stylish commute. It’s perfect for those crisp autumn days or any time you want a smart-casual look that doesn't sacrifice comfort.

6. Brown Ribbed Knit Top + Brown Flared Leggings + Faux Fur Leopard Print Cropped Jacket + Brown Suede Heeled Boots

Brown Ribbed Knit Top + Brown Flared Leggings + Faux Fur Leopard Print Cropped Jacket + Brown Suede Heeled Boots
Brown Ribbed Knit Top + Brown Flared Leggings + Faux Fur Leopard Print Cropped Jacket + Brown Suede Heeled Boots

This outfit is giving me major cozy-glam vibes, honestly! It's that perfect blend of comfy loungewear meets 'I'm ready for a night out.' It feels super chic but also incredibly relaxed, like you could wear it anywhere and feel amazing. I love how it’s all about warm, earthy tones, making it feel so sophisticated and put-together.

The Outfit: I like to start with these super comfy brown ribbed knit flared leggings. They're so flattering and have that perfect amount of stretch.

Then, I've paired them with a simple, matching brown ribbed knit top. It creates this seamless, elongated silhouette. To really elevate it and add that touch of glam, I've thrown on this amazing faux fur leopard print cropped jacket. It’s the statement piece that brings everything together and adds so much texture.

Finally, we finish it off with these chic brown suede heeled boots. They have a pointed toe and a block heel, which looks so sleek with the flared leggings.

Accessories you can pair: To keep the focus on the outfit, I'd suggest some delicate gold hoop earrings and maybe a simple gold pendant necklace.

A structured crossbody bag in a neutral tone like black or cream would be perfect. You could also add a thin brown leather belt if you want to cinch the waist a bit more, but honestly, I think it looks great as is!

Why this works? This combo is a winner because of the mix of textures and the monochromatic color scheme. The soft knit of the leggings and top feels so luxurious, while the faux fur adds a fun, playful element.

The flared silhouette is super on-trend, and pairing it with a heeled boot makes your legs look miles long. It’s a look that’s both comfortable and fashion-forward.

Best for: I see this outfit being perfect for a stylish brunch with friends, a casual date night, or even just running errands when you want to feel extra fabulous. It's also great for a weekend getaway or exploring a new city. It's that versatile look that makes you feel confident and chic, no matter what you're up to.

7. Black Satin Corset Top + Black Flare Leggings + Black Pointed Toe Heels

Black Satin Corset Top + Black Flare Leggings + Black Pointed Toe Heels
Black Satin Corset Top + Black Flare Leggings + Black Pointed Toe Heels

Honestly, this combo? Pure perfection! It's giving total siren energy, you know? Like, you walk into a room and everyone just notices. It's sophisticated, a little bit daring, and just has this amazing power vibe that makes you feel like you can conquer anything. I just love how sleek and put-together it looks, without trying too hard at all. It's the kind of outfit that makes a statement all on its own.

The Outfit: I've paired a stunning Black Satin Corset Top with some super comfy Black Flare Leggings. The corset is everything; it gives that amazing sculpted silhouette with that gorgeous sheen. It’s structured in all the right places, making you feel super confident.

And then, the flare leggings! They're the perfect contrast, creating this long, lean line that's just incredibly flattering. I like to make sure the leggings hit right at the ankle, or even slightly longer, so they perfectly drape over the shoes.

The Black Pointed Toe Heels are the cherry on top, elongating your legs even further and adding that extra touch of glam.

Accessories you can pair: For accessories, I'd keep it pretty minimal to let the outfit shine. Maybe a delicate silver or gold chain necklace, nothing too chunky.

A small clutch bag would be perfect. If you want a bit more edge, maybe a sleek black belt over the corset, but honestly, it’s stunning without it.

Why this works? This outfit is a masterclass in contrasting textures and silhouettes. You've got the structured, shiny satin of the corset against the soft, stretchy fabric of the leggings. The fitted top paired with the dramatic flare at the bottom creates this dynamic shape that’s just so captivating. It’s effortlessly chic and screams confidence.

Best for: This look is honestly perfect for a night out! Think fancy dinner dates, cocktails with your friends, or even a special event where you want to feel a little extra. It’s also amazing for feeling super glam while keeping comfortable.

8. Beige Linen Blazer + Taupe Satin Camisole + Black Flared Trousers + Tan Strappy Heels

Beige Linen Blazer + Taupe Satin Camisole + Black Flared Trousers + Tan Strappy Heels
Beige Linen Blazer + Taupe Satin Camisole + Black Flared Trousers + Tan Strappy Heels

Honestly, this combo? Pure perfection if you're aiming for that effortlessly chic, sophisticated vibe with a hint of allure. It’s the kind of outfit that makes you feel put-together and confident, like you just stepped out of a high-fashion magazine. It balances professional polish with a touch of feminine softness, making it super versatile.

The Outfit: Let's break it down. I love starting with these sleek Black Flared Trousers. They’re so flattering and give off a really polished, elongated silhouette, especially when paired with heels.

Then, I like to layer a delicate Taupe Satin Camisole underneath. The luxe sheen of the satin totally elevates the whole look and adds that subtle touch of glamour that we all love.

And to top it off, a sharp Beige Linen Blazer. The relaxed yet structured feel of the linen blazer adds a sophisticated layer that just ties everything together beautifully. It's the perfect contrast to the soft satin.

Accessories you can pair: To really finish this off, I'd suggest some delicate gold jewelry – maybe a dainty necklace and some stud earrings. A structured crossbody bag or a chic clutch would be perfect.

And of course, those Tan Strappy Heels are just divine; they add a touch of elegance without being too much. They literally complete the entire ensemble.

Why this works? This outfit works because it’s all about the contrast and balance. You’ve got the structured blazer against the soft cami, the classic black trousers with the elegant satin, and the neutral tones that just sing together. It’s a masterclass in elevated basics that look incredibly chic and intentional.

Best for: This look is honestly perfect for so many occasions! Think a stylish brunch, a sophisticated date night, or even a more relaxed business casual setting. It’s also fabulous for when you want to feel a little dressed up but still super comfortable.

9. Yellow Cotton Crew Neck T-Shirt + Blue Denim Jacket + Navy Flared Leggings + Tan Leather Loafers

Yellow Cotton Crew Neck T-Shirt + Blue Denim Jacket + Navy Flared Leggings + Tan Leather Loafers
Yellow Cotton Crew Neck T-Shirt + Blue Denim Jacket + Navy Flared Leggings + Tan Leather Loafers

Okay, so this outfit? It's giving me all the cool, casual, and super comfy vibes. It’s the perfect blend of relaxed and put-together, you know? Like you just threw it on, but you still look effortlessly chic. It’s that go-to look when you want to feel good and look put-together without trying too hard. Honestly, I love it when an outfit feels this easy!

The Outfit: I like to start with these amazing Navy Flared Leggings. They're so flattering and comfortable, and the flare adds such a fun, retro touch.

On top, I'd pair a simple Yellow Cotton Crew Neck T-Shirt. The pop of yellow is so cheerful and brightens up the whole look! Then, I love to layer a classic Blue Denim Jacket over it. It’s the perfect casual outerwear that just pulls everything together so well.

For shoes, I've picked out these Tan Leather Loafers. They add a touch of polished sophistication and tie in beautifully with the casual vibe.

Accessories you can pair: To finish this off, I'd suggest some simple silver stud earrings, nothing too flashy. A tan crossbody bag would also look super cute and practical. If you want a little extra flair, maybe a delicate chain necklace. It’s all about keeping it minimal but chic.

Why this works? This combination just works because of the perfect balance between comfort and style. The flared leggings bring a trendy silhouette, while the denim jacket and tee ground the look with classic, casual pieces. The loafers add that sophisticated touch that elevates it from just loungewear to a stylish outfit.

Best for: This is literally your perfect weekend warrior outfit! I’d wear this for running errands, grabbing coffee with friends, a casual movie date, or even just lounging at home but still wanting to feel cute. It’s also great for travel days when comfort is key but you still want to look your best.

10. White Cotton Button-Up Shirt + Forest Green Knit Flare Leggings + Brown Leather Loafers

White Cotton Button-Up Shirt + Forest Green Knit Flare Leggings + Brown Leather Loafers
White Cotton Button-Up Shirt + Forest Green Knit Flare Leggings + Brown Leather Loafers

Honestly, this combo is giving me major chic and comfy vibes! It’s that perfect blend of polished yet relaxed, like you just effortlessly threw it on but still look totally put-together. You know that feeling when an outfit just clicks? That’s this! It’s ideal for someone who loves to look stylish without sacrificing comfort, making it a total win for everyday wear.

The Outfit: I like to start with these amazing Forest Green Knit Flare Leggings. They’re super flattering and the flare is just perfect!

Then, I pair them with a classic White Cotton Button-Up Shirt. I love rolling up the sleeves like this to give it a more casual, laid-back feel. It’s the perfect contrast to the fitted leggings.

Accessories you can pair: To finish this look, I'd personally add a rich Brown Leather Tote Bag. It adds a lovely warm tone and is super practical.

And for shoes, you can’t go wrong with Brown Leather Loafers. They tie everything together and keep the look grounded and sophisticated.

Why this works? This outfit is a masterclass in balance! The relaxed fit of the oversized shirt against the sleek, form-fitting leggings creates a really appealing silhouette.

Plus, the rich green and crisp white is such a sophisticated color combination, and the brown leather accessories add just the right amount of warmth and texture. It’s basically effortless elegance.

Best for: I can totally see you rocking this for a casual brunch date, running errands in style, or even a relaxed day out exploring the city. It’s also perfect for those days when you want to feel a bit dressed up but still want to lounge comfortably. Seriously, it’s a go-to for so many occasions!

11. Cream Cable Knit Sweater + Brown Flared Leggings + Taupe Suede Boots

Cream Cable Knit Sweater + Brown Flared Leggings + Taupe Suede Boots
Cream Cable Knit Sweater + Brown Flared Leggings + Taupe Suede Boots

Okay, so you know that feeling when an outfit is just perfect? That's this one! It's giving effortless chic meets cozy comfort, like you just threw it on but still look totally put together. It’s perfect for those days when you want to feel comfy but still want to look amazing.

The Outfit: I love starting with these super soft brown flared leggings. They're that perfect rich, chocolatey brown and the flared leg is just so flattering, right?

I like to pair them with a creamy, chunky cable knit sweater. The texture contrast between the smooth leggings and the cozy knit is just everything. It’s the perfect balance of fitted and relaxed.

Accessories you can pair: To finish this off, I'd personally go for some taupe suede ankle boots. The color ties in perfectly with the sweater, and the suede adds a touch of texture.

For jewelry, I'd keep it simple, maybe a delicate gold necklace and some small hoop earrings. A structured crossbody bag in a neutral tone like beige or black would complete the look.

Why this works? Honestly, this combo is pure perfection because of the color palette and the silhouette. The warm neutrals are so grounding and chic, and the flare of the leggings balances the relaxed fit of the sweater. It’s a classic combination that’s always stylish.

Best for: This outfit is literally perfect for a weekend brunch, a casual day of running errands, or even a relaxed coffee date. It’s comfy enough for lounging but stylish enough to make a statement wherever you go.

12. Green Collared Cardigan + Black Flared Leggings + Black Mary Jane Heels

Green Collared Cardigan + Black Flared Leggings + Black Mary Jane Heels
Green Collared Cardigan + Black Flared Leggings + Black Mary Jane Heels

This outfit is giving me such chic, academia vibes! It's effortlessly polished yet super comfortable, making it perfect for anyone who wants to look put-together without trying too hard. You know that feeling when an outfit just clicks? This is totally it, a perfect blend of classic style with a modern, relaxed silhouette. It's the kind of look that makes you feel confident and ready for anything.

Let's break it down. We've got this gorgeous Green Collared Cardigan, which is seriously a showstopper. I love the crisp white trim, it adds such a sophisticated contrast. It buttons up to a neat collar, giving it that collegiate charm.

Then, we're pairing it with classic Black Flared Leggings. These aren't just any leggings; they have that lovely flare at the bottom that balances out the fitted top perfectly and elongates your legs like magic!

For accessories, I'd totally go with some simple silver hoop earrings to keep the look clean and sophisticated. A structured black crossbody bag would also be super chic and practical.

You could even add a delicate silver necklace if you wanted a little extra sparkle, but honestly, this look shines on its own.

What makes this combo work so well is the play between the fitted, structured top and the relaxed, flowing bottoms. The bold green is super trendy and eye-catching, while the black leggings keep it grounded and versatile. It's that perfect mix of preppy and comfy-chic that’s just amazing!

This outfit is honestly best for a casual day on campus, a stylish brunch date, or even running errands when you want to look extra polished. It’s perfect for those days when you want to feel a bit preppy but still super comfy.

13. Grey Washed Graphic Sweatshirt + Black Flare Leggings + White and Grey Suede Sneakers

Grey Washed Graphic Sweatshirt + Black Flare Leggings + White and Grey Suede Sneakers
Grey Washed Graphic Sweatshirt + Black Flare Leggings + White and Grey Suede Sneakers

Okay, you know that effortlessly cool vibe that just screams 'I woke up like this, but make it fashion'? That's exactly the energy this outfit is giving off! It's comfy, it's casual, but it has this undeniable cool factor that's just perfect for a laid-back day.

The Outfit: We're starting with these amazing black flare leggings, honestly, the perfect base for almost anything. They hug you just right and then flare out beautifully, giving you that retro-cool silhouette.

On top, I've paired them with this super soft, grey washed graphic sweatshirt. It’s got this awesome vintage feel with the graphic print and the washed-out color, making it feel really unique and personal.

And to finish it off, we have these classic white and grey suede sneakers. They keep the look grounded and add that perfect sporty-chic touch.

Accessories you can pair: To really nail this look, I'd keep the accessories minimal. Maybe a simple silver chain necklace or a couple of delicate rings.

A black crossbody bag would be super practical and stylish, or if you're feeling it, a cute baseball cap could add an extra layer of cool. Honestly, with this combo, less is more!

Why this works? This outfit is a masterclass in balancing comfort and style. The flare leggings bring a touch of drama to the casual sweatshirt, while the washed-out graphic tee adds personality without being over the top.

The sneakers tie it all together with a relaxed, everyday feel. It’s the kind of outfit that looks put-together without trying too hard, hitting that sweet spot between cozy and chic.

Best for: I can totally see you rocking this look for a casual weekend brunch, running errands on a Saturday, or even just lounging at home when you want to feel a little extra stylish. It's also perfect for travel days when comfort is key but you still want to look good. It’s basically your new go-to for any relaxed occasion.

14. Grey Fuzzy Knit Sweater + Grey Flared Leggings + Black Leather Pumps

Grey Fuzzy Knit Sweater + Grey Flared Leggings + Black Leather Pumps
Grey Fuzzy Knit Sweater + Grey Flared Leggings + Black Leather Pumps

Honestly, this combo? It's giving off major chic, relaxed vibes, and I am obsessed. It’s that perfect blend of cozy comfort meeting polished sophistication. You know that feeling when an outfit just clicks? This is it! It’s effortlessly cool, making you feel put-together without even trying. The whole look is super sleek and modern, perfect for when you want to feel a little fancy but stay comfy.

The Outfit: Let's break it down! I love how the Grey Fuzzy Knit Sweater is so soft and has that slightly relaxed fit, which is the perfect contrast to the more fitted Grey Flared Leggings. The leggings themselves? They’re amazing because they have that subtle flare that just elongates your legs and adds a touch of retro flair.

And the Black Leather Pumps? They are the ultimate finishing touch, adding that polished edge that takes this from comfy-casual to seriously stylish.

Accessories you can pair: To really elevate this, I’d personally add a simple silver pendant necklace, nothing too flashy, just a little sparkle.

A structured black crossbody bag would also look super chic, or you could totally rock the clutch shown. Keep the jewelry minimal to let the outfit shine.

Why this works? This outfit works because it plays with textures and proportions. The soft, fuzzy knit of the sweater balances the sleek, smooth fabric of the leggings. Plus, the flared silhouette of the pants paired with the pointed-toe pumps creates such a flattering and elongating effect. It’s a monochromatic dream that’s anything but boring!

Best for: I can totally see you rocking this for a casual Friday at the office, a stylish brunch with friends, or even a relaxed evening out. It’s also perfect for travel if you want to look chic while staying super comfy on the go.

15. Cream Silk Blouse + Brown Corduroy Flared Trousers + Camel Wool Coat

Cream Silk Blouse + Brown Corduroy Flared Trousers + Camel Wool Coat
Cream Silk Blouse + Brown Corduroy Flared Trousers + Camel Wool Coat

This outfit is pure cozy sophistication! It gives off such a warm, autumnal vibe, like you're ready for a thoughtful afternoon browsing a bookstore or enjoying a mellow coffee date. It’s effortlessly chic and feels so put-together without being fussy, you know? It's the kind of look that makes you feel instantly polished and ready for anything.

The Outfit: I just love how the Cream Silk Blouse drapes so beautifully, adding a touch of understated glam. It’s so smooth and luxurious!

Then, we have these amazing Brown Corduroy Flared Trousers. The corduroy texture is just perfect for fall, and the flare silhouette is so flattering and adds a retro-cool feel.

To top it all off, I've paired it with a classic Camel Wool Coat. It’s the perfect neutral layer, bringing everything together with a sophisticated, timeless touch. The fringe detail on the coat adds a little something extra, too!

Accessories you can pair: To keep the sophisticated vibe going, I'd suggest some delicate gold jewelry, maybe a simple pendant necklace and some stud earrings. A structured leather crossbody bag in a deep burgundy or a classic tan would be amazing.

And for shoes, the suede ankle boots you see here are perfection, but you could also totally rock some loafers.

Why this works? Honestly, this combo is a masterclass in texture and complementary colors. The smooth silk against the ribbed corduroy is divine, and the warm camel and brown tones are just SO autumnal and harmonious. It’s a sophisticated play on cozy fall essentials that just clicks.

Best for: This outfit is ideal for those crisp fall days. I can totally picture you wearing this to a lovely brunch, a relaxed day of shopping, or even a casual work setting where you want to feel a bit more dressed up. It’s perfect for any occasion where you want to feel warm, stylish, and effortlessly put-together.

16. Cream Ribbed Knit Sweater + Royal Blue Velvet Flared Leggings + Tan Trench Coat

Cream Ribbed Knit Sweater + Royal Blue Velvet Flared Leggings + Tan Trench Coat
Cream Ribbed Knit Sweater + Royal Blue Velvet Flared Leggings + Tan Trench Coat

Okay, you know that feeling when an outfit just clicks? It's chic, it's comfortable, and it makes you feel ready for anything, even a little rain! This look is all about that sophisticated yet super relaxed vibe. It’s perfect for when you want to look put-together without trying too hard, giving off major effortless cool-girl energy that I just love.

The Outfit: I've started with these amazing royal blue velvet flared leggings, seriously, the color is so rich and the velvet texture is divine! They hug you in all the right places and then flare out beautifully.

On top, I've paired them with a super soft cream ribbed knit sweater. It's got that cozy, classic feel that balances the boldness of the leggings perfectly.

And to tie it all together, we've added a classic tan trench coat. It’s the ultimate layering piece, adding structure and a touch of timeless elegance to the whole ensemble.

Accessories you can pair: To keep this look polished, I'd suggest some sleek black pointed-toe heels, like the ones shown, to really elongate the legs. A simple black leather crossbody bag would be functional and stylish.

For jewelry, maybe some delicate gold hoops or a simple pendant necklace, nothing too over-the-top, we want the outfit to shine!

Why this works? Honestly, this combo is pure perfection. The flared leggings add a fun, retro silhouette, while the cream sweater and tan trench coat bring in that classic sophistication. The textures velvet, knit, and trench fabric create depth, and the color contrast between the royal blue and cream is just striking. It’s a look that's both trendy and timeless.

Best for: This outfit is ideal for a stylish day out running errands, a casual lunch with friends, or even a relaxed city exploration. It's perfect for those transitional weather days when you need a stylish layer but want to stay comfortable and chic. You'll look amazing wherever you go!

17. Sage Knit Wrap Top + Sage Flared Leggings + Nude Ballet Flats

Sage Knit Wrap Top + Sage Flared Leggings + Nude Ballet Flats
Sage Knit Wrap Top + Sage Flared Leggings + Nude Ballet Flats

This outfit is all about that effortless, chic comfort. It gives off major 'lounging in style' vibes, perfect for when you want to look put-together without trying too hard. It's laid-back but still has that little something extra, you know? Like you just threw it on, but it’s always the right choice.

The star here, for me, are these gorgeous Sage Flared Leggings. I love how they hug you just right and then flare out so gracefully, it’s such a flattering silhouette.

Paired with this equally soft Sage Knit Wrap Top, which has this lovely tie detail at the front, it creates a really cohesive and comfy look. The wrap style is super forgiving and adds a touch of femininity.

I also like that the knit texture on the top adds a bit of dimension against the smoother fabric of the leggings.

To keep the vibe super chill and cohesive, I’d suggest minimal accessories. Maybe some delicate gold hoop earrings to add a little sparkle near your face, and perhaps a simple crossbody bag for practicality.

You could also tie your hair up in a messy bun to really lean into that relaxed feel, or let it flow if you’re feeling a bit more done up. Just keep it simple; the outfit speaks for itself!

Honestly, this combo just works because of the matching color palette and the complementary silhouettes. The soft knit top balances the structured flare of the leggings, and the monochromatic look is inherently elongating and chic. It’s proof that comfort and style can absolutely go hand-in-hand without compromising on either, giving you that relaxed yet polished aesthetic.

I think this outfit is perfect for a cozy day at home, running errands when you want to feel a bit more elevated, or even for a casual brunch with friends. It’s that go-to look for when you want to feel comfy, confident, and effortlessly stylish. You'll basically live in it!

18. Olive Ribbed Knit Sports Bra + Olive Ribbed Knit Flare Leggings + Beige Knit Duster Cardigan

Olive Ribbed Knit Sports Bra + Olive Ribbed Knit Flare Leggings + Beige Knit Duster Cardigan
Olive Ribbed Knit Sports Bra + Olive Ribbed Knit Flare Leggings + Beige Knit Duster Cardigan

Honestly, this combo gives off such a effortlessly chic and comfy vibe, you know? It's that perfect blend of athletic-inspired cool with a touch of laid-back sophistication. It’s the kind of look that says, “I’m put-together, but I’m also ready to relax or conquer my day.” It’s super flattering and just feels so good on.

Let's break it down! We've got this amazing olive ribbed knit sports bra, it's supportive but still super sleek. I love how it pairs with the matching olive ribbed knit flare leggings. The flares are everything, seriously! They balance out the silhouette and give it that retro-yet-modern feel.

Then, to top it off, I like to add this flowy, open-front beige knit duster cardigan. It adds such a soft, relaxed layer and just drapes beautifully, making the whole outfit feel elevated and intentional.

For accessories, I'd keep it simple. Maybe some delicate gold hoop earrings and a simple pendant necklace would be perfect. You could also totally rock a crossbody bag for a casual vibe or a chic tote if you're heading somewhere a bit more polished.

And of course, clean white sneakers are a must for that sporty-chic finish!

This outfit totally works because of the monochromatic base with the olive set. It’s super elongating and chic! The ribbed texture adds interest, and the contrast of the fitted top and bottom with the flowing duster cardigan creates a really dynamic and balanced silhouette. It's proof that comfort and style can absolutely go hand-in-hand.

I think this look is perfect for running errands, grabbing brunch with friends, traveling, or even just lounging at home when you want to feel a little extra. It’s that versatile, go-to outfit that’s always a winner!

Olive Ribbed Knit Sports Bra + Olive Ribbed Knit Flare Leggings + Beige Knit Duster Cardigan

For a slightly different take, you can swap the beige duster for an olive knit duster cardigan to go for a fully monochromatic look! It really streamlines the whole silhouette and makes the outfit feel like a cohesive, intentional set. Plus, there's just something so calming and chic about wearing all one color, it's the ultimate "quiet luxury" vibe while staying completely comfy.

19. Burgundy Mineral Wash Cotton Tee + Burgundy High-Waisted Flared Leggings

Burgundy Mineral Wash Cotton Tee + Burgundy High-Waisted Flared Leggings
Burgundy Mineral Wash Cotton Tee + Burgundy High-Waisted Flared Leggings

Okay, you know that feeling when an outfit just clicks? It’s effortless, comfy, but still totally put-together. That's exactly the vibe I'm getting from this look! It's that perfect blend of relaxed chic with a hint of retro cool, thanks to those flared leggings. Honestly, it’s the kind of outfit that makes you feel good from the moment you put it on, whether you're running errands or meeting friends for a casual brunch.

The Outfit: Let's talk pieces! I love how the Burgundy Mineral Wash Cotton Tee has that super soft, lived-in feel. It's not just a basic tee; the mineral wash gives it texture and a slightly moody hue that’s just perfect.

I like to pair it with the Burgundy High-Waisted Flared Leggings. These aren't your average leggings, either. The high waist is super flattering, and that flare at the bottom? Pure 70s magic! The matching color makes it look almost like a stylish one-piece.

Accessories you can pair: To really elevate this, I'd personally go for some chunky silver hoops. They’ll pop against the rich burgundy. A black leather crossbody bag would add a nice contrast and keep your hands free.

For shoes, a simple black sneaker or even a cool lug-sole boot like the ones shown would totally nail the vibe.

Why this works? This combo is a winner because it's all about comfort meeting style. The monochromatic look is incredibly elongating and chic, while the mineral wash tee adds just enough casual interest. It’s proof that you don't need a lot of pieces to make a big statement. It’s simple, it’s effective, and it just feels right.

Best for: I see this outfit being perfect for those days when you want to look stylish but prioritize comfort. Think weekend getaways, casual shopping trips, or just a relaxed day out. It’s also fantastic for travel because it’s basically fancy loungewear!

20. Cream Satin Button-Up Shirt + Grey Flared Leggings + Grey Pointed-Toe Heels + Grey Wool Coat

Cream Satin Button-Up Shirt + Grey Flared Leggings + Grey Pointed-Toe Heels + Grey Wool Coat
Cream Satin Button-Up Shirt + Grey Flared Leggings + Grey Pointed-Toe Heels + Grey Wool Coat

Honestly, this outfit gives off such a chic and sophisticated vibe, I absolutely love it for you! It’s that perfect blend of polished professionalism with a touch of cozy comfort, making it ideal for days when you want to look put-together without feeling restricted. You'll totally radiate confidence and effortless style.

Let's break it down: I like to start with these amazing Grey Flared Leggings. They offer that flattering silhouette that hugs you in all the right places while giving a subtle flare at the bottom, which I find so elongating.

Then, I'd pair that with a Cream Satin Button-Up Shirt. The silky fabric just drapes beautifully, adding that touch of luxe against the comfy leggings.

And you absolutely have to top it off with this Grey Wool Coat. It's the perfect finishing layer, giving the whole look a refined, almost boss-babe feel. The color palette is just divine, so neutral and classic!

For accessories, I'd suggest keeping it sleek. Maybe some delicate silver earrings, like tiny hoops or studs, would be perfect. A structured tote bag in a complementary grey or black would tie it all together seamlessly.

And of course, those gorgeous Grey Pointed-Toe Heels are a must. They complete the polished silhouette and elevate the entire ensemble. It's all about understated elegance here, you know?

This outfit just works because it perfectly balances soft, comfortable fabrics with sharp, tailored lines. The flared leggings and pointed heels create a streamlined shape, while the satin blouse and wool coat add texture and a sophisticated sheen. It’s a masterclass in how to look incredibly stylish while prioritizing comfort, aligning with that modern, busy woman vibe we all aspire to.

I see this look being absolutely perfect for a stylish day at the office, especially if you have client meetings or a presentation. It’s also fantastic for a chic lunch date or even a sophisticated evening out where you want to feel a bit more dressed up. Basically, anywhere you want to feel powerful and polished!

21. Cream Silk Button-Up Shirt + Brown Knit Cardigan + Charcoal Heather Flared Leggings + Brown Leather Loafers

Cream Silk Button-Up Shirt + Brown Knit Cardigan + Charcoal Heather Flared Leggings + Brown Leather Loafers
Cream Silk Button-Up Shirt + Brown Knit Cardigan + Charcoal Heather Flared Leggings + Brown Leather Loafers

Honestly, this combo just screams effortless chic! It’s got this comfy-yet-put-together vibe that I’m totally loving. You know those days when you want to look super stylish but also feel like you're wearing your comfiest clothes? Yeah, this is that outfit. It's perfect for when you want to feel polished without even trying, like you just threw it on and still look amazing.

The Outfit: I like to start with these Charcoal Heather Flared Leggings. They're so comfy and that flare adds a touch of retro cool that I adore.

On top, I'd pair a Cream Silk Button-Up Shirt. The silky texture is such a luxe contrast to the casual leggings, and I love how it drapes.

Then, I'd layer on this super cozy Brown Knit Cardigan. It’s the perfect finishing touch, adding warmth and a lovely textured element that pulls everything together.

And to tie it all off, you can't go wrong with these classic Brown Leather Loafers. They’re super comfy and give off that sophisticated, understated vibe.

Accessories you can pair: For accessories, I’d keep it simple to let the outfit shine. A delicate gold necklace would look so pretty peeking out from the neckline of the silk shirt.

You could also add a structured leather crossbody bag in a deep tan or black to keep your essentials handy. Maybe even a simple watch to complete the look.

Why this works? This outfit is a masterclass in balancing textures and silhouettes. The soft, slightly slinky feel of the silk top contrasts beautifully with the more textured knit of the cardigan and the cozy fabric of the flared leggings.

The flare of the leggings adds a flattering shape, and the relaxed fit of the cardigan makes it feel super approachable and cozy. It’s a perfect blend of comfort and subtle sophistication.

Best for: I think this outfit is amazing for a relaxed weekend brunch, running errands in style, or even a casual day at the office if your workplace is more laid-back. It's also fantastic for travel days when you want to look good but feel incredibly comfortable on a long journey.

22. Cream Oversized Button-Up Shirt + Terracotta High-Waisted Flared Leggings + Tan Leather Loafers

Cream Oversized Button-Up Shirt + Terracotta High-Waisted Flared Leggings + Tan Leather Loafers
Cream Oversized Button-Up Shirt + Terracotta High-Waisted Flared Leggings + Tan Leather Loafers

Honestly, this combo? Pure perfection for that effortless, chic vibe that just screams 'I have my life together, but I'm also super relaxed about it.' It’s that go-to look that’s comfortable enough for errands but stylish enough for a casual brunch. It’s all about that sophisticated ease, you know?

The Outfit: I'm starting with these amazing Terracotta High-Waisted Flared Leggings – they're seriously a dream! The color is so rich and earthy, and the high waist is super flattering.

Then, I like to pair them with a Cream Oversized Button-Up Shirt. I've cuffed the sleeves to keep it looking polished and not too sloppy. This shirt is made from a lovely lightweight fabric, which makes the whole look feel airy and sophisticated.

Accessories you can pair: To finish it off, I'd suggest some Tan Leather Loafers. They add just the right touch of classic style without being fussy.

And honestly, you can't go wrong with a simple Canvas Tote Bag. It’s practical and keeps the whole vibe grounded and casual.

Why this works? This outfit works because it perfectly balances comfort and style. The flared leggings give you that trendy silhouette, while the oversized shirt offers a relaxed yet put-together feel. The neutral color palette, cream, terracotta, and tan is just timeless and always looks incredibly chic. It's a look that feels intentional without trying too hard.

Best for: I feel like this is your ultimate weekend outfit. Think farmer's market runs, meeting friends for coffee, or even a casual day trip. It’s also perfect for travel because you’ll be so comfortable but still look super put-together.

23. Blue Stripe Button-Down Shirt + Camel Single-Breasted Blazer + Sage Green High-Waisted Flared Leggings

Blue Stripe Button-Down Shirt + Camel Single-Breasted Blazer + Sage Green High-Waisted Flared Leggings
Blue Stripe Button-Down Shirt + Camel Single-Breasted Blazer + Sage Green High-Waisted Flared Leggings

Okay, you know that feeling when an outfit is just perfect? This look totally gives off that effortlessly chic, I've-got-it-all-together vibe, but with a super comfy twist. It's that perfect blend of professional polish and laid-back cool, making you feel ready to conquer anything, from a client meeting to a leisurely brunch.

The Outfit: I love starting with these fantastic sage green high-waisted flared leggings. Seriously, they're the foundation of this whole stylish ensemble! They hug you in all the right places and that flare? It's so flattering and adds a touch of retro glam.

Then, I'd layer a classic blue stripe button-down shirt underneath. You can leave a few buttons undone for a relaxed feel, which I always do!

To top it off, I'd throw on a sophisticated camel single-breasted blazer. It instantly elevates the whole look and ties everything together beautifully. It’s the ultimate power pairing, honestly.

Accessories you can pair: For accessories, I'd keep it simple and chic. Think delicate gold jewelry, like a subtle necklace or some small hoop earrings. A structured crossbody bag or a chic tote would be perfect.

And of course, you need some comfortable yet stylish shoes! A pointed-toe flat or a low block heel in a neutral shade, like nude or tan, would totally complete this look.

Why this works? This combo is a total winner because it plays with proportions and textures. The sleek leggings contrast perfectly with the structured blazer, and the classic shirt adds a timeless touch. It’s that elevated casual look that feels modern and so put-together. Plus, the color palette is just gorgeous, don't you think?

Best for: Honestly, I see this outfit working for so many occasions. It’s perfect for a business casual office setting, a stylish lunch date, or even just running errands when you want to feel a bit more dressed up. You could even wear this on a weekend city break!

24. Cream Cable Knit Sweater + Burgundy Flared Leggings

Cream Cable Knit Sweater + Burgundy Flared Leggings
Cream Cable Knit Sweater + Burgundy Flared Leggings

Honestly, this combo? Pure perfection! It gives off this cozy-chic vibe that's just perfect. It’s the kind of look that feels put-together without trying too hard, you know? It’s effortlessly stylish and perfect for when you want to feel comfy but still look totally on point.

Let's break it down. I love pairing this super soft cream cable knit sweater. The texture of the knit adds so much depth and warmth, and the cream color is just a classic.

Then, we've got these amazing burgundy flared leggings. They are everything! The rich, deep burgundy color is so sophisticated, and the flare at the bottom is just so flattering. They hug you in all the right places and then flow beautifully.

For accessories, I’d totally add a delicate gold necklace, something simple to complement the neckline of the sweater.

And maybe a structured crossbody bag in a neutral tone, like tan or black, to keep the look grounded. Oh, and a pair of simple gold hoop earrings would be fabulous too!

What makes this outfit work is the balance. The relaxed fit of the cozy sweater is perfectly complemented by the sleek, form-fitting nature of the leggings. Plus, the contrast between the chunky knit texture and the smooth fabric of the leggings is just so good. It’s a modern take on a classic silhouette that feels totally fresh.

This look is absolutely perfect for a casual weekend brunch, a relaxed day of running errands when you want to feel fabulous, or even a cozy movie night. You'll look amazing wherever you go!

25. Black Long Sleeve Zip Top + Chocolate Brown Flared Leggings + Brown Leather Ankle Boots

Black Long Sleeve Zip Top + Chocolate Brown Flared Leggings + Brown Leather Ankle Boots
Black Long Sleeve Zip Top + Chocolate Brown Flared Leggings + Brown Leather Ankle Boots

This outfit is honestly giving me such a cool, laid-back yet put-together vibe. It’s that perfect blend of comfort and subtle style, you know? It’s the kind of look that screams effortless chic, like you just threw it on but still managed to look amazing. It’s super versatile, and I feel like it would flatter pretty much everyone because it’s so balanced.

The Outfit: I love starting with these chocolate brown flared leggings; they’re just perfect. The flared silhouette is so flattering and brings a touch of retro flair, plus the fabric looks super comfy.

On top, I’ve paired it with a sleek black long-sleeve zip-up top. The black balances the warmth of the brown perfectly, and the zip detail adds a little something extra without being too much.

Then, to finish it off, I’ve added these classic brown leather ankle boots. They tie the whole look together and give it a bit of an edge.

Accessories you can pair: Honestly, you don’t need much with this! I’d personally keep accessories minimal. Maybe a simple gold chain necklace to add a subtle sparkle near the neckline, or a black crossbody bag to keep things practical. If you want a bit more personality, a tan leather belt could look super cute cinched over the leggings, but I also love it just as is.

Why this works? This combination works because of the perfect balance between the fitted top and the flared bottoms, creating a really flattering silhouette. The color palette is so grounded and earthy, which feels really sophisticated. It’s a modern take on a classic look, blending comfort with a dash of trendiness thanks to those flares.

Best for: I see this outfit being perfect for a casual weekend outing, like running errands or grabbing coffee with a friend. It’s also great for travel days when you want to be comfy but still look stylish. You could even dress it up slightly for a casual dinner date, especially if you add a bit of jewelry.

26. Olive Green Jersey Flared Leggings + Cream Jersey Tank Top + Olive Green Jersey Blazer

Olive Green Jersey Flared Leggings + Cream Jersey Tank Top + Olive Green Jersey Blazer
Olive Green Jersey Flared Leggings + Cream Jersey Tank Top + Olive Green Jersey Blazer

Okay, you know that feeling when you want to be comfy but still look super put-together and chic? This outfit is literally that feeling, bottled up and ready to go! It’s got this effortless, sophisticated vibe that’s perfect for when you need to look polished without trying too hard. Honestly, it’s the kind of look that makes you feel confident and ready for anything, whether you're running errands or meeting friends for lunch.

The Outfit: I love how we've started with these amazing Olive Green Jersey Flared Leggings. They're so comfy, but the flare gives them a dressier feel than your average leggings, you know? They really balance out the look perfectly.

On top, I've paired them with a simple Cream Jersey Tank Top. It’s a classic, neutral base that lets the other pieces shine. And to tie it all together, we've added an Olive Green Jersey Blazer. It’s structured enough to look professional but the jersey fabric keeps it super relaxed and comfortable, mirroring the leggings. It's basically the perfect blend of comfort and style.

Accessories you can pair: To keep this look polished yet casual, I’d suggest some delicate gold jewelry maybe a simple pendant necklace and some small hoop earrings. A structured crossbody bag in a neutral tone like beige or taupe would be absolutely perfect.

And if you wanted to elevate it just a touch more, a pair of sleek black loafers or even some clean white sneakers would work wonders!

Why this works? This combo is a winner because it plays with proportions and textures so well. The flared leg of the leggings is balanced by the structured blazer, and the monochromatic color scheme in olive green with a cream contrast is just prefect. It’s modern, comfortable, and undeniably chic. It aligns with that 'elevated casual' vibe we're all loving right now.

Best for: I can totally see you rocking this look for a weekend brunch, a relaxed day at the office if your workplace is more casual, or even for a stylish travel outfit. It’s that versatile piece that you'll reach for again and again when you want to look good and feel amazing.

Conclusion

So there you have it! We've gone through how to rock flared leggings for literally any occasion, from super chill vibes to something a little more dressed up.

Honestly, the best part about flares is how darn versatile they are. They’re like the comfy, stylish chameleon of your wardrobe! I really hope this gives you some fun ideas to play around with.

You’ve totally got this, and I have a feeling you'll discover some amazing new looks that make you feel so good.

Go ahead, give these outfits a whirl, you'll probably surprise yourself with how much you love them! Happy styling, my friend!

Loving This Guide? Get More Like This! 💌

Want to impress with clothes? Want to look good? Subscribe to Whatsmyshape Newsletter and get weekly fashion guides, exclusive outfit ideas, and beauty tips delivered directly to your inbox. No spam, just pure style inspiration! ✨