Winter Styling Tips I Learned From My Favorite Street Style Regulars

Icy temps are no match for these outfit ideas.

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winter street style outfit

At the time of writing this, I’m wearing the same oversized sweater I’ve had on — more or less — for the past two months, a pair of spandex shorts, wool socks, and nary a shoe in sight. To paraphrase, I am not trying all that hard to get dressed up at the present moment. New York City’s winter chill combined with yet another COVID-19 wave has kicked nearly all style ambitions out the door. But settling in at my desk and beginning a new year of work projects and travel plans, it's come to my attention that there is a proverbial hole my spandex simply can’t fill. I want to get dressed up again. And I suspect I'm not alone here.

The solution to this quandary is always the same — find that spark of inspiration. For me, this usually entails thumbing through magazines or clicking through photo galleries of street style photographs. The latter is especially helpful when it’s an everyday outfit you’re after. So, in the spirit of giving our wardrobes the old college try that they deserve this winter (perhaps the hardest of the four seasons to get dressed during, I might add), continue ahead for 10 looks from my favorite street style regulars like Julia Sarr Jamois and Veronika Heilbrunner and hopefully pick up a new idea or two to ease that transition to wearing ‘real’ clothes again.

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Julia Sarr Jamois

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If one of your 2022 style resolutions was to dress more expressively this year, then take note of Julia Sarr Jamois, British Vogue’s fashion director. In this cold weather look, she infuses a pair of traditional slacks with contemporary context by styling it with a printed top and furry-trim coat. If you own similar trousers that are typically relegated to interviews or snoozy work presentations, follow her lead and bring them back to life with a couple of splashy separates.

Natasha Goldenberg

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Feathers aren’t the first texture you reach for when the weather app shows below 40 degrees — but that should probably change. Ditch the everyday wool scarf and wrap up in a celebratory strand of feathers for a lively take on dead-of-winter dressing. Keep the rest of the look simple, like a black jacket and trousers, and finish with a pair of low heels or your favorite sneakers.

Jenny Walton

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Rethink the puffer coat this winter and pick one in an exuberant color and long length, like Jenny Walton’s. The street style regular proves that sometimes the coat is the look, and all that’s left for a strong outfit are a few smart accessories, like a pair of statement earrings and some fun shoes.

Tamu McPherson

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Photographer and all-around stylish human Tamu McPherson is a seemingly bottomless well of clever outfit ideas. Here, she shows how to dress up a jumpsuit by layering a white top underneath, leather coat on top, and a silk scarf fashioned à la babushka to finish. A tasteful look you can keep toasty in.

Gabriella Karefa-Johnson

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Gabriella Karefa-Johnson’s covetable style is like a shot of adrenaline — colorful, energetic, and lacking any adherence to antiquated style rules. This winter, emulate her take on print mixing by styling a plaid coat with a pair of check-patterned pants. Underneath, team with a graphic tee to tie the look together (if it’s especially cold out, don't forget the heat tech base layers!).

Camille Charriere

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For days when you might prefer not to fuss with layers, the secret to a chic look can be surprisingly simple. This outfit, courtesy of Camille Charriere, shows the power of a really great accessory; a scarf strategically knotted over an elegant long coat — and that's it. Complemented by a pair of slouchy leather boots, it’s the kind of ensemble that will never feel outdated.

Alexandra Carl

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It’s hard to pinpoint why denim-on-denim is so unfailingly chic, but as Alexandra Carl illustrates, it just is. This season, style your jeans (bonus points if they’re wide-leg) with a denim shirt and accessorize with a leather belt to help differentiate the two. On top, a long and dramatic camel coat to bring it all together.

Virginia Smith

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Vogue’s Virginia Smith has the kind of style superpower where she can take a timeless piece and effortlessly elevate it. In the case of this cold-weather look, a chunky knit paired with trousers in a similar tone manages to nail the sleek, understated vibe with ease. The lesson to be learned here is slouchy silhouettes coupled with a neutral (but interesting!) color palette is the ticket.

Veronika Heilbrunner

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A brightly colored puffer jacket is a pretty easy way to cheer up your winter style, but if you’re looking for another way to wear it than with jeans, try Veronika Heilbrunner's monochrome approach and pair yours with a sweater in the same color — the effect is attention-grabbing and works for any sort of setting, both formal and casual.

Jan-Michael Quammie

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There are no bad outfit days in Jan-Michael Quammie’s world, it seems, and this wintry look is worth a repeat. Begin with a ruffle-neck top, followed by a tie-dye tee, completed by a leather blazer with a matching pair of pants. Next, add in a long trench coat and finish things off with brightly colored accessories, like cat-eye sunglasses and a handbag. Et voila — a dynamic but not at all difficult ensemble to reboot your cold-weather style.