32 Winter Outfits to Wear When You're Bored of Your Clothes

Thinking ahead to winter, all the pieces you’ll be pulling out of storage, and the new items you’ll be adding to your cold-weather wardrobe? Same, same, and same. While I live in L.A., where the weather never really dips into freezing temps, I always transition my outfits based on the season. Plus, I have some upcoming travels to more winter-inclined climates that have me thinking about lots of coats and layers.

In need of some inspiration to put me in the mindset of winter outfits for the months ahead, I rounded up some looks from Instagram and the street style scene that I’m sharing here today. These are styling ideas I want to put into effect as soon as the weather allows. Ahead, get some inspiration for yourself. I’ve organized the winter outfits by category so you can scroll down to see the coolest ways to style boots, dresses, hats, and everything in between.

OUTFITS WITH BOOTS

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(Image credit: @thora_valdimars)

Tuck your trousers into knee-high boots.

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(Image credit: @kerrypieri)

Or opt for tights and a blazer with tall boots.

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(Image credit: @carodaur)

Black ankle boots are a winter essential.

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(Image credit: @_jeanettemadsen_)

See how versatile they are?

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(Image credit: @louloudesaison)

Pair sock boots with an ankle-grazing coat.

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OUTFITS WITH SNEAKERS

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(Image credit: @thefashionguitar)

Chunky sneakers are the style to own.

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(Image credit: @claire_most)

Or go for a more classic sneaker style.

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OUTFITS WITH HEELS

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(Image credit: @brooketestoni)

Heels are the perfect complement to a pantsuit. This is a cool spin on a holiday party outfit.

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(Image credit: @thestylestalkercom)

You can also wear heels for the day with a trench.

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OUTFITS WITH DRESSES

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(Image credit: @thestylestalkercom)

Try a bold pattern.

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(Image credit: @pandorasykes)

Style a colorful dress with colorful boots.

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(Image credit: @pernilleteisbaek)

Or layer neutrals together.

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(Image credit: @thestylestalkercom)

Cowboy boots are the style every fashion girl is wearing this season.

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OUTFITS WITH SKIRTS

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(Image credit: @fionazanetti)

Wear a metallic skirt with a leather jacket for a cool holiday look.

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(Image credit: @adenorah)

A miniskirt with tights and boots is French girl–approved.

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OUTFITS WITH SWEATERS

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(Image credit: @deborabrosa)

Winter is the time to pile on your cozy sweaters.

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(Image credit: @ada_oguntodu)

Try a monochrome look.

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(Image credit: @sophiaroe)

Opt for a more fitted style to layer underneath outerwear.

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OUTFITS WITH COATS

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(Image credit: @lpeopleswagner)

When it comes to puffer coats, the bigger the better.

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(Image credit: @alwaysjudging)

Oversize coats are everywhere this season.

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(Image credit: @styleheroine)

Yellow is a cool and unexpected color for winter.

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(Image credit: @sabinasocol)

Make a statement in a faux-fur coat.

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(Image credit: @nycbambi)

White on white on white.

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OUTFITS WITH HATS

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(Image credit: @camillecharriere)

Tap into Parisian style with a beret.

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(Image credit: @champagnemani)

Another case for trying the cool hat.

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(Image credit: @thestylestalkercom)

And another.

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(Image credit: @thestylestalkercom)

You can also try a wide-brim style.

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OUTFITS WITH JEANS

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(Image credit: @emilisindlev)

Try jeans with a loose fit.

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(Image credit: @chrissyford)

This denim-on-denim look is suited for milder winter climates.

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OUTFITS WITH PANTS

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(Image credit: @thestylestalkercom)

Break out the corduroys.

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(Image credit: @thestylestalkercom)

Yes, leggings are making a comeback.

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(Image credit: @thestylestalkercom)

As are wide flares.

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Next: six winter shopping picks our editors all agree on.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.