It’s Leggings-and-Flats Season—These Are the Combinations That Look the Chicest Right Now

Try as I might, every morning I go to my wardrobe with the intention of wearing a skirt or trousers, but I inevitably step away with a pair of leggings in hand.
Honestly, I can't seem to tear myself away from them—but really, why would I want to? With a comfortable fit and sleek silhouette, they are the only thing I wear to wear right now. Naturally, when I'm wearing my leggings at home, I pair them with fluffy socks and slippers; and when I do leave the house, I want to retain the same comfort levels I experience indoors, but with a more elegant payoff.
Freshly inspired by the surprisingly chic leggings-and-flat-shoe outfits I've seen in recent weeks, I've curated an edit of the most elevated leggings and flats combinations to wear this season. Scroll on to see them.
4 CHIC LEGGINGS-AND-FLAT-SHOE OUTFITS TO TRY
1. LEGGINGS + MARY JANES
Style Notes: An unexpected but highly elegant combination, leggings and Mary Janes are a chic (and very French) two-piece outfit I'll keep coming back to. I'll pop on some socks if I need to keep my feet cosy, but if the sun is shining, I'll often go without.
SHOP LEGGINGS AND MARY JANES:
2. LEGGINGS + KNEE-HIGH BOOTS
Style Notes: A classic leggings and tall boots outfit is one of the chicest ways to wear leggings, in my opinion. To add to the elegance, style with a wool coat or blazer, otherwise pair with an oversized knit for a low-key look.
SHOP LEGGINGS AND KNEE-HIGH BOOTS:
Simple riding boots are a wardrobe staple you'll never tire of.
I always come back to The Row for its luxe basics.
3. LEGGINGS + LOAFERS
Style Notes: Over the past few seasons, simple leather loafers have become an absolute pillar of my wardrobe. Smart enough to polish up the most casual look, leggings and loafers are an unexpected combination I'll keep reaching for throughout the coldest season.
SHOP LEGGINGS AND LOAFERS:
Style with sleek loafers or dress these up with a pointed-toe heel.
In my opinion, Marks and Spencer's basics are some of the best out there.
4. LEGGINGS + TRAINERS
Style Notes: Leggings and trainers are a classic pairing for a reason. Ideal for zipping around during a day of errands, this easy combo will keep you comfortable for hours. For a modern silhouette, pair with tall white socks and accessories with a pair of shades.
SHOP LEGGINGS AND TRAINERS:
Salomon trainers are a fashion-person favourite.
Taekwondos are set to be a major trainer trend next season.

Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.
With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.
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