What to Wear With Flare Leggings?

Flare leggings are making a significant comeback, and for good reason – this retro silhouette is flattering, comfortable, and incredibly versatile. The slightly flared leg provides balance and elongates the leg line, while the stretchy fabric hugs your curves. You can wear flare leggings for various occasions, from running errands to going out with friends. Just pair them with the right top and footwear, and you’ve got an effortlessly chic outfit. Here are 30 stylish ways to wear flare leggings.

Table of Contents

Casual Daytime Outfits

Casual Daytime Outfits

Flare leggings are ideal for casual daytime activities like meeting friends for brunch or spending a day shopping. Pair your leggings with simple tops and footwear for these types of outings.

1. Flare Leggings with Hoodie and Sneakers

A hoodie and sneakers create a relaxed, sporty vibe. Opt for a fitted zip-up hoodie that contrasts with the color of your leggings. Complete the outfit with white or neutral sneakers. This look works well for running errands or meeting friends for an easygoing brunch.

2. Flare Leggings with T-Shirt and Slip-On Shoes

An oversized, graphic t-shirt balances the form-fitting leggings. Slip-on shoes like loafers, mules, or ballet flats make the outfit appropriate for daytime activities. Add a crossbody bag and sunglasses to finish this casual chic look.

3. Flare Leggings with Sweater and Ankle Boots

Pair your leggings with an oversized, slouchy sweater or cardigan. Choose one that hits at hip level to accentuate your waist. Then add ankle boots for a bit of height and polish. This is a go-to fall or winter outfit for looking put together.

4. Flare Leggings with Denim Jacket and Sneakers

A denim jacket brings a casual, retro vibe to flare leggings. Contrast the fitted bottom with a relaxed-fitting jacket. White or neutral sneakers keep the look lowkey. You can also switch out the denim jacket for a jean vest.

5. Flare Leggings with Cropped Sweatshirt and White Sneakers

Pair them with a cropped sweatshirt to show off your leggings’ flare silhouette. Tuck the front into your leggings, allowing the flare to peek underneath. Then, ground the outfit with classic white sneakers, which elongate the leg.

Going Out Looks

When you want to look stylish for a night out, flare leggings easily transition for the evening. Dress them up with heels, blazers, and flashy accessories.

6. Flare Leggings with Silk Cami and Heels

Elevate flare leggings for nighttime with a silky camisole tank. Look for one with delicate straps, lace trimming, or a cowl neckline. Pair it with strappy heels or block heels. Finish with a wristlet clutch, and you’re ready for girls’ night!

7. Flare Leggings with Lace Bodysuit and Booties

A lace bodysuit looks sexy and dressy with flare leggings. Choose one with long sleeves or a plunging V-neckline. Then slip on ankle booties or over-the-knee boots. Add statement earrings, a cuff bracelet, and bold lips for a night-out ensemble.

8. Flare Leggings with Satin Blouse and Pumps

Wear your leggings with a satin blouse for cocktails or date nights. Go for a bold color or print to make it more festive. Tuck the blouse in neatly and add pointed-toe pumps. This dressier option works for many social occasions.

9. Flare Leggings with Sequin Top and Sandals

Make a sparkling statement by pairing leggings with a sequin tank or crop top. Keep accessories minimal to let the top shine. Strappy, high-heeled sandals balance the volume on top with a leg-lengthening silhouette.

10. Flare Leggings with a Blazer and Block Heels

Transform your flare leggings into business casual attire with a tailored blazer and block heel booties. This stylish option works for after-work events or nights with colleagues. Finish with a crossbody bag.

Work-Appropriate Outfits

Work-Appropriate Outfits

Believe it or not, flare leggings can be office-appropriate with the proper styling. Choose thick, opaque leggings in dark colors like black, navy, or forest green. Then, balance the look with tunics, blazers, and ballet flats for a professional vibe.

11. Flare Leggings with Tunic and Ballet Flats

A tunic top is critical for making flare leggings office-ready. Look for one that hits mid-thigh with long sleeves. Pair it with classic ballet flats in black or nude. This combination creates a chic, polished look for casual offices.

12. Flare Leggings with Blouse and Smoking Slippers

For a desk-to-dinner outfit, tuck an elegant silk blouse into leggings. Blouses with ruffle detailing, a bow-tie neck, or a keyhole cut-out add visual interest. Then slip into velvet smoking slippers, which offer comfort while looking pulled together.

13. Flare Leggings with a Sweater Dress and Ankle Boots

Turn heads in a knit sweater dress layered over leggings. Look for one with long sleeves and a hem that hits just above the knee. Complete the outfit with ankle boots or booties. It’s a fashionable look for offices with a relaxed dress code.

14. Flare Leggings with a Blazer and Loafers

A fitted blazer on top counterbalances the flare leggings’ silhouette. Opt for a neutral color like black, beige, or gray. Finish the professional look with menswear-inspired loafers. This powerhouse outfit means business.

15. Flare Leggings with Kimono Top and Ballet Flats

A kimono-style top adds coverage and visual interest. Choose one that ties at the waist to define your shape. Pair it with simple black ballet flats for the office. Then, switch the apartments out for strappy heels to transition it for happy hour.

Athleisure Looks

Athleisure Looks

Flare leggings are ideal for low-impact workouts and athleisure wear. Style them with layering pieces like hoodies, long vests, and oversized sweaters. Sneakers or slip-on shoes complete the sporty vibe.

16. Flare Leggings with Sports Bra and Sneakers

Show off your style at the gym by pairing leggings with a colorful strappy sports bra—layer on an unbuttoned flannel or denim shirt. Then, finish with supportive sneakers. This athleisure outfit works for anything from yoga to meeting friends after a workout.

17. Flare Leggings with Tank and Hoodie

Running errands after the gym? Throw on a drapey tank with a built-in shelf bra and a zip-up hoodie. Top with a baseball cap and sneakers for an easygoing, sporty style. Don’t forget your gym bag!

18. Flare Leggings with Oversized Sweater and Slip-Ons

Conceal your workout wear under an oversized, slouchy sweater. Choose one that extends past your hips to conceal your leggings waistband. Then, complete the outfit with slip-on sneakers or slides. This incognito look works when you want comfy clothes after the gym.

19. Flare Leggings with Long Vest and Beanie

Layer a lightweight puffer or quilted vest over your leggings and sports bra. The long silhouette maintains coverage while showing off the flare. Top with a beanie for chilly weather walks, hikes, or runs.

20. Flare Leggings with a Cropped Hoodie and high tops

A cropped hoodie puts a sporty twist on classic leggings. Pair it with chunky high-top sneakers like Converse Chuck Taylors. This relaxed pairing works well for casual activities like walking the dog or running errands.

Seasonal Looks

Seasonal Looks

Flare leggings are a year-round staple. Adapt them for warmer or colder temperatures by layering them accordingly.

21. Flare Leggings with Tank and Kimono (Spring/Summer)

A kimono adds coverage while allowing airflow for hot weather. Pair it with a breezy tank or camisole. This effortless combination works for spring and summer activities like picnics or day dates.

22. Flare Leggings with a Crop Top and Jacket (Spring/Summer)

Show some skin in a cropped tank or tee under an unbuttoned jean jacket. This outfit balances sexiness and coverage for warm weather. Complete the look with strappy sandals.

23. Flare Leggings with Poncho and Ankle Boots (Fall/Winter)

Stay cozy in a chunky poncho sweater paired with your leggings. Choose one with a turtleneck or mock neck for extra warmth. Then, ground the voluminous top with heeled ankle booties. This outfit mixes textures while keeping you warm.

24. Flare Leggings with Oversized Sweater and Beanie (Fall/Winter)

An oversized fisherman sweater provides head-to-toe warmth and comfort. Add a slouchy beanie and furry boots to complete this winter-ready ensemble. The big top helps balance the leggings’ fitted silhouette.

Maternity Looks

Flare leggings are ideal for growing bumps. Adapt these maternity-friendly suggestions as your body changes.

25. Flare Leggings with Flowy Tunic and Sandals

A flowy tunic provides bump coverage and breathability for expecting moms. Pair with supportive slide sandals for an effortless maternity outfit. Switch the sandals out for slippers or sneakers for activities like baby appointments or prenatal yoga.

26. Flare Leggings with a Wrap Dress and Flats

A wrap dress adjusts beautifully over a growing bump. Belt it above your belly and pair it with ballet flats for an easy maternity outfit. This combination works for casual activities or can be dressed up for maternity photos.

27. Flare Leggings with Maternity Tee and Cardigan

Swap restrictive tops for soft, stretchy maternity tees. Layer a long, open cardigan over the tee to balance proportions. Then, slip on slippers or sneakers for all-day comfort. This casual look works well for pregnant mamas.

28. Flare Leggings with a Tank Dress and Sandals

Show off your bump in a form-fitting maternity tank dress. Choose one with side ruching or a wrapped silhouette. Pair it with your favorite leggings for coverage and comfort. Complete the outfit with supportive slide sandals or slip-ons.

Plus Size Outfit Ideas

Plus Size Outfit Ideas

Flare leggings are incredibly flattering for curvy figures. Accentuate your shape with fitted or flowing tops.

29. Flare Leggings with Drapey Blouse and Pumps

A fluid, asymmetric blouse cinches the waist while draping over curves. Tuck it in neatly and add pumps to lengthen the legs. This polished outfit works for both work and evenings out.

30. Flare Leggings with Empire Waist Dress and Sandals

An empire waist dress accentuates the slimmest part of your torso. Choose a knit dress for stretch and comfort. Pair with flat sandals or slides to keep the look casual. The full skirt balances the leggings’ fit.


What shoes look best wear with flare leggings?

  • Sneakers or slip-on shoes for casual looks
  • Ankle booties or pumps for dressier occasions
  • Sandals in warm weather
  • Ballet flats for the office

What tops pair well with flare leggings?

  • Tunic tops and sweater dresses provide coverage
  • Cropped and tucked-in tees show off the flare
  • Drapey blouses and kimonos add visual interest
  • Sweaters and hoodies create cozy, casual outfits
  • Blazers make them work-appropriate

Can you wear flare leggings to work?

Yes, with the proper styling. Opt for thick, opaque leggings in dark colors. Pair them with tunics, blazers, cardigans, and ballet flats for a polished look. They work best in casual offices.

Are flare leggings dressier than skinny leggings?

Yes! The flared leg silhouette elongates the leg line, creating a more polished look. Pair them with heels and blouses or bodysuits for nighttime wear.

What outfits can you wear with flare leggings during pregnancy?

Flowy dresses and tunics, maternity tees, wrap dresses, and tank maternity dresses all pair well with flare leggings during pregnancy. They provide comfort with adjustable room for your growing bump.


Flare leggings have made a major comeback in the fashion world, and they are not just a passing trend. These versatile leggings are gaining popularity because of their ability to seamlessly transition from workout wear to stylish outfits for work or a night out. The key to their versatility is how they can be styled. With the right top and accessories, flare leggings can create a chic and sophisticated look without sacrificing comfort.

They are also a great option for those who want to add a touch of flair to their wardrobe without going overboard. So, whether you’re headed to the gym, running errands, or attending a social event, these leggings are a perfect choice. Discover six things to avoid wearing with leggings to ensure your flare leggings always look their best. Use the tips in this article to help you create 30 chic, comfortable looks with your favorite pair of flare leggings, allowing you to mix and match to find options that perfectly suit your style and mood!

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