Chicago's Best Winter Street Style In 25 Chic Snaps!

If you thought a Chicago winter was all about parkas and skull caps, get ready to have your world rocked. We hit the (frozen) streets to find out how Chicago faces the colder months with sartorial fierceness, and, as usual, the Windy City didn't let us down. 25 unbelievably chic street-style photos are just a click away. So, see if you can spot your friends, and some local style stars, too. Whether our snaps inspire, motivate, or just impress you, we can all agree that even the most intense winter days can't stop Chicago style from heating things up.
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When Penny's not working at Sofia in the Gold Coast, she's a walking example of how to accessorize for both form and function, even on the gnarliest days.


Photographed by Amy Creyer
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Laura is a style blogger and Conde Nast marketing staffer with serious skills, and she's proving them with creative layers in neutral (not boring!) hues.


Photographed by Amy Creyer
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Monika's voluminous Opening Ceremony coat caught our eye from across the street. As for her bag, it was completely refreshing to see someone carrying such sweetness during mean weather.


Photographed by Amy Creyer
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Sarah is a student at Columbia who's style savvy and confidence allow her to pull off a seriously huge vintage fur hat. Her layers and winter-perfect Coach boots are so Chicago.


Photographed by Amy Creyer
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We were really impressed by all of the belted coats that came out to our open call shoot, but this was one of our favorites. A rich mauve color is one we're not getting sick of any time soon.


Photographed by Amy Creyer
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Rhianna is a Chicago native visiting home from Tufts University. We're fully appreciating her bold lip on a dreary day, as well as her balanced outfit focusing the volume on top. That scarf by the way, was thrifted in Paris. Yeah.


Photographed by Amy Creyer
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Anna is a style blogger you're probably quite familiar with. We love the classic, chic personal style she sticks to, no matter the weather. Those boots are Chloe, and yes, we want them, too.


Photographed by Amy Creyer
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Aramide is a style blogger and wardrobe stylist in Chicago. Her boots and coat are a perfect example of how to bring sweet femininity to your winter wardrobe.


Photographed by Amy Creyer
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Jan is a staffer at Chicago's Trunk Club, and came to our shoot in a J. Crew coat that proves a point: Your outerwear can be the star of your outfit, if you're not afraid of something bold and bright.


Photographed by Amy Creyer
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Can we talk about the fierce model face Bridget has managed to pull off during a snowstorm? Work!


Photographed by Amy Creyer
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Dan is a sales associate at Burton, hence the rad coat. His Analog hat is a collaboration with Burton, too.


Photographed by Amy Creyer
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Jenny is an engineering intern in the city, who also has a hidden talent for finding vintage accessories, apparently.


Photographed by Amy Creyer
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Sheetal Patel designs G.I.A. Luxe bags, but she caught our eye because of that gorgeous belted coat.


Photographed by Amy Creyer
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Erin Brennan of StyleBlock showed up to our shoot in a vintage cape that renewed our faith in outerwear. We love that she's illustrating our point about cool winter hats, too.


Photographed by Amy Creyer
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Kristin's Burberry earmuffs were a birthday gift from several (very) sweet friends. She's keeping her Wellies in rotation this winter by pairing them with ultra-thick, comfy socks.


Photographed by Amy Creyer
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eDrop-Off owner Corri McFadden doesn't even notice it's freezing outside. She's got a Balenciaga jacket and super-sized fur hat to keep her warm.


Photographed by Amy Creyer
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Jackie Trezzo's outfit was so inspiring, we went shopping at Sofia Boutique right after this shoot! Her whole look is from Sofia, with the exception of her AllSaints coat. Love the drama.


Photographed by Amy Creyer
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We weren't letting Marc get away without a photo in that Versace for H&M coat. We're totally into Dr. Martens on guys this winter. Are you?


Photographed by Amy Creyer
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After your Chicago editor finished staring at her Valentino bag, she chatted up Jena Gambaccini on her C/FAN hood. Everything about Jena's look is purposeful, warm, and stunning.


Photographed by Amy Creyer
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Your Chicago editor Shani loves the functionality of her Coach bag on gross days when getting around the city can be hard. Her favorite winter hat du jour was a $1 thrifting find!


Photographed by Amy Creyer
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Ashley, not surprisingly, works and shops at Crossroads, where she scored most of her look. We love how her outfit mixes textures and color while looking polished.


Photographed by Amy Creyer
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Amy works in ad sales in Chicago, when she's not blowing our minds in wedge boots (they're Jil Sander!).


Photographed by Amy Creyer
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We love Whitney's Urban Outfitters boots (and the deal she scored on them!). The fact that we love her almost-all-black look isn't shocking–she's a Refinery29 Chicago intern.


Photographed by Amy Creyer
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Nikia, a.k.a. ChiTownFashionista, found a chic belted coat (it's ASOS), that's just as much a part of her look as what's underneath it.


Photographed by Amy Creyer
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Chelsea Lavin of eDrop-Off came out to see us in a pair of Charlotte Ronson pants we'd wear all winter. She's smartly paired them with a great Rag & Bone heel to keep the outfit from looking too casual. This look is must-copy.


Photographed by Amy Creyer
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