17 Casual Winter Outfits That Are Elite in Every Way

Well, friends, it looks like we're gearing up for another season of this new normal, and seeing as certain dressier looks have felt off to us all year, we think it's our duty to serve up a fresh round of outfit ideas that actually feel relevant for the times. I think we can all agree that casual and easy-to-throw-together looks are what we want to wear the most right now, whether it be some elevated loungewear for chilling at home or a composition of cool basics that look chic no matter what.

But just because you're wearing something casual and comfortable doesn't mean your outfit can't also look elevated and cool. In fact, sometimes wearing your standard basics can be really stylish. We've found that the trick comes down to a few key style staples and picking out the right accessories to add in. Yep, even when wearing something as simple as jeans and sneakers. Want to see some chic fashion person–approved ideas? Go on to check out 17 casual winter outfits that are elite in every way.


(Image credit: @claire_most)

PSA: There's a new neckline in town, and it's about to replace all your basic tops.

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(Image credit: @sylviemus_)

How to spice up your simplest outfits? Drape a contrasting knit sweater over any outerwear, from a blazer to a coat, for a preppy vibe that feels so right now.

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(Image credit: @sofiamcoelho)

Lightweight layers are always a good idea, and we're giving this combo of a turtleneck, loose trousers, and a trench coat an A+.

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(Image credit: @champagnemani)

A not-so-basic sweater and retro sneakers are a surefire way to make your sweatpants look more "fashion."

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(Image credit: @nlmarilyn)

Try a ribbed-knit dress when you don't know what else to wear. It's easy and comfortable and always looks so polished. 

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(Image credit: @amaka.hamelijnck)

Trousers are a winter staple on their own, and we're loving how fresh they look here with a chunky sweater and retro sneakers.

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(Image credit: @mimi.orere)

A blazer-inspired coat instantly makes any loungewear ensemble look more pulled-together.

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(Image credit: @emilisindlev)

Try relaxed leather pants instead of jeans for your next coffee run. A bright puffer coat brings the look to life.

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(Image credit: @erinoffduty)

Since I know you're probably on the hunt for more chic legging looks at the moment, here's another French girl–approved take.

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(Image credit: @sophiabrenn)

Knit sets are the loungewear trend the fashion set is obsessed with at the moment.


(Image credit: @CHRISSYFORD)

Throw on a second-skin top to liven up your jeans.

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(Image credit: @fakerstrom)

Sometimes, less is more, and this perfect outfit made up of just the basics is proof.

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(Image credit: @lenafarl)

A grandma sweater is cool and guaranteed to earn your compliments. 

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(Image credit: @tamaramory)

Leather pants are the perfect base to all your favorite sweaters right now.

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(Image credit: @slipintostyle)

Leaving the house in your sweats? A teddy coat and chunky boots instantly add style.

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(Image credit: @jen_wonders)

Layer a plain T-shirt underneath a sweater-vest for a casual take on the trendy knit.

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Next up, 30 Holiday Gifts I Secretly Want for Myself

Senior Editor

Anna is an editor on the fashion team at Who What Wear and has been at the company for over five years, having begun her career in the Los Angeles office before relocating to New York, where she's currently based. Having always been passionate about pursuing a career in fashion, she built up her experience interning at the likes of Michael Kors, A.L.C., and College Fashionista before joining the team as a post-graduate assistant editor. Anna has penned a number of interviews with Who What Wear's cover stars over the years, including A-listers Megan Fox, Issa Rae, and Emma Chamberlain. She's earned a reputation for scouting new and emerging brands from across the globe and championing them to our audience of millions. While fashion is her main wheelhouse, Anna led the launch of WWW Travels last year, a new lifestyle vertical that highlights all things travel through a fashion-person lens. She is passionate about shopping vintage, whether it be at a favorite local outpost or an on-the-road discovery, and has amassed a wardrobe full of unique finds. When she's not writing, you can find her shooting street imagery on her film camera, attempting to learn a fourth or fifth language, or planning her next trip across the globe.