Leggings are comfortable, versatile, and when styled right, they look incredibly chic. If you’re wondering how to wear leggings beyond the gym or your couch, you’ve come to the right place.
These leggings outfit ideas show you exactly how to style flared leggings with everything from oversized sweaters to leather jackets.
From casual weekend looks to outfits for running errands or meeting friends for coffee, keep scrolling for 28 ways to make leggings look intentional and stylish.
1. Crop Top and Oversized Button Up
Start with a fitted crop top and matching flared leggings for a streamlined base. Throw on an oversized button up shirt left open for that perfect casual layer. The contrast between the fitted leggings and loose shirt creates great proportions.
Finish with your favorite sneakers for an outfit that works for brunch or shopping trips.
2. Leather Jacket with Shearling Collar
A leather jacket with a shearling collar makes flared leggings look expensive. The texture combination of smooth leather, fluffy shearling, and stretchy leggings creates visual interest.
Wear this on transitional weather days when you need something cozy but still want to look cool.
3. White Ribbed Crop Top and Black Leggings
A white ribbed crop top with black flared leggings creates perfect contrast. Add white athletic shoes to tie the look together. The ribbed texture adds just enough detail without trying too hard.
4. Sleeveless Crop Top and Sneakers
For warmer days, wear a white sleeveless crop top with black flared leggings and crisp white sneakers. This outfit is both sporty and cute.
Wear it for casual outings when you want to look put together without sacrificing comfort.
5. Oversized Denim Jacket and Knit Scarf
Layer an oversized denim jacket over your flared leggings and add a chunky knit scarf for texture.
The denim adds structure to the stretchy leggings while the scarf brings in cozy elements. Perfect for chilly morning coffee runs.
6. Cream Oversized Knit Sweater
An oversized cream knit sweater with black flared leggings is cozy chic at its best. Find a sweater that hits at just the right spot on your hips. Too long and you lose your shape. Too short and you miss that oversized vibe.
7. Gray Sweatshirt and White Sneakers
Keep things casual with a gray sweatshirt tucked slightly into black flared leggings. White sneakers keep the look fresh and modern. This outfit looks intentional while being completely comfortable.
8. Striped Button Up Shirt
A striped button up shirt brings preppy vibes to your flared leggings. Leave a few buttons undone at the bottom and tie the shirt at your waist for a relaxed feel. Sneakers keep this look grounded and wearable.
9. White Polo Shirt
A white polo with black flared leggings and white sneakers creates an unexpectedly chic combination. The structured collar of the polo elevates the casual nature of leggings instantly.
10. Striped Knit Sweater and Baseball Cap
A white and cream striped knit sweater looks amazing with black flared pants. Add white sneakers and top it off with a black baseball cap for sporty casual vibes. Athletic inspired pieces can still look polished.
11. Cropped Blouse
Dress up your flare leggings with a cropped blouse. The structured fabric of a blouse contrasts nicely with stretchy leggings. This combination works when you need something between casual and dressy.
12. Black Long Sleeve Crop Top
Going all black with a long sleeve crop top and black flare leggings creates a sleek monochromatic look. The cropped length adds shape to an otherwise streamlined outfit. Add statement accessories or keep things minimal.
13. White Strapless Asymmetrical Top
A white strapless asymmetrical top paired with black flare leggings makes a statement. The interesting neckline and asymmetrical hem bring drama to a simple outfit. Great for evening plans when you want to dress up your leggings.
14. Black Blazer and Crop Top
Transform black flare leggings into office appropriate attire by adding a black crop top and a tailored black blazer. The blazer makes leggings look professional while the crop top keeps things modern.
This all black ensemble always looks put together.
15. Striped Sweater and Denim Jacket
Layer a white striped sweater under a light wash denim jacket and pair with black flare leggings. White sneakers complete this balanced casual look. The mix of textures and classic color combination works every time.
16. Camel Textured Knit Sweater
A camel colored textured knit sweater brings warmth to black flare leggings. The neutral tone is sophisticated while the texture adds visual interest. White sneakers keep the look casual and modern.
17. Bikini Top and Leather Jacket
For edgy style, try a black bikini top under a black leather jacket with black flare leggings. White chunky sneakers add an unexpected sporty element. This outfit is about confidence and making a statement.
18. Brown Oversized Sweater with Satin Leggings
Match a brown oversized sweater with brown satin flare leggings for a luxe monochromatic moment. The satin fabric elevates regular leggings into something special. Tonal dressing always looks expensive and thoughtful.
19. Sleeveless Button Up Vest
A white sleeveless button up vest brings preppy sophistication to black flare leggings. White pointed flats keep the look polished rather than sporty. Great for when you want to wear leggings but need something slightly more formal.
20. Floral Printed Blouse
Add personality with a floral printed blouse paired with flare leggings. White pointed flats maintain the feminine vibe. The print brings life to solid leggings while keeping the outfit grounded and wearable.
21. Off Shoulder Top and Pointed Heels
Dress up black flared pants with a white off shoulder top and white pointed heels. The bare shoulders add a romantic touch while heels elongate your legs. Leggings absolutely work for date night.
22. Black Puffy Vest and Converse
Layer a black puffy vest over a black fitted top with black flared pants. Black Converse sneakers complete this all black athletic inspired look. The vest adds dimension and warmth without bulk.
23. Tank Top and Oversized Denim Shirt
Start with a beige tank top and black flared pants, then layer an oversized denim shirt on top. White sneakers keep things casual.
The neutral tank prevents the denim from overwhelming the outfit while allowing for that oversized shirt moment.
24. Wrap Style Long Sleeve Top
A white wrap style long sleeve top creates beautiful lines when paired with black flared leggings. White chunky sneakers add a modern touch. The wrap detail brings sophistication to casual leggings.
25. Cream Sweatshirt
A cream sweatshirt with black flared leggings and white sneakers is casual comfort at its best. The light top and dark bottom combination is universally flattering and always looks fresh.
26. Ribbed Crop Top and Denim Jacket
Mix things up with a white ribbed crop top, blue denim jacket, and camel flared pants. White sneakers tie all the neutral tones together. This unexpected color combination feels fresh while being totally wearable.
27. Quarter Zip Athletic Top
A quarter zip athletic top with flared pants and white athletic shoes creates the perfect sporty look. The zip detail adds interest while maintaining that athletic aesthetic. Ideal for days when you actually are heading to or from the gym.
28. Oversized Button Up and Leather Loafers
A cream oversized button up shirt paired with black flared leggings and black leather loafers creates instant sophistication. The loafers elevate leggings from casual to chic.
This outfit works for casual Fridays or weekend brunches where you want to look polished but feel comfortable.
