Does winter fashion exist in Chicago? ‘Project Runway’ designer weighs in

Winter in Chicago is a beast all its own. The biting wind, the icy streets, and the bone-chilling temperatures make it nearly impossible to focus on anything other than survival. And yet, every winter, my social media feeds are flooded with influencers’ winter outfits with unzipped jackets, paper-thin sweaters, and shoes that are clearly not salt-proof. It’s cute for the camera, but let’s be real–it’s not cutting it in the Windy City.

For those of us trudging through slush puddles and bracing against the wind-tunnel effect downtown, the challenge becomes this: Is it possible to stay warm and fashionable in this city, or are we doomed to choose practicality over looks? 

To get some expert insight, I turned to Peach Carr, Chicago native and designer, whose fashion sense has graced the screens of “Project Runway” season eight and “All Stars.”

“I’m no stranger to the wind and the cold,” Carr said. “The wind is just ridiculous, but what I look forward to when it gets cold is layering. My personal favorite is taking a T-shirt and layering it under a big oversized sweater. I’ll belt it over some trousers or jeans, throw a scarf on, and maybe add my Chanel brooch. It’s chic, interesting, and still warm.”

Her advice couldn’t be more relevant. So many of us fall into the trap of bulky, shapeless coats and clunky snow boots that scream “practical,” but Carr insists we don’t have to choose between function and flair. Carr suggests freshening up the sometimes depressing sea of gray and black coats with accessories.

 “There are so many great boots out there that are all-weather without being big and clunky,” Carr said. “A wool or puffer coat with a pop of color, like red or purple gloves, can make an outfit fun while keeping you warm,” she explained. “I love those hats with the big pom-poms or the photographer-style headbands. Just something fun.”

But for me, it is not only a struggle to look cute outside, but deal with all Chicago’s bars and restaurants that are not guaranteed to have coat check, leaving me dragging my giant coat during nights out. 

Carr’s solution is, once again, layering, to keep the outfit fun for the night out–but not to freeze on the way there.

 “I have a client who wears bustiers with pearls or rhinestones and pairs them with a blazer or a wrapped cashmere sweater, a pencil skirt, and cute boots. You’re layered, but there’s still a chic, sexy look to it,” she said.

The only thing I would add to her outfit suggestion is to get an Uber so you don’t have to deal with the weather for more than two minutes between the bar and the car door.

Carr also warns against underestimating the power of basics. “A cashmere turtleneck in black or camel can go with everything—jeans, skirts, trousers. Add a scarf or a brooch, and you look like a million bucks,” she says.

Her final advice? Put in the effort. “Tim Gunn, who’s a good friend of mine, always said, ‘If you look like you care, you look great.’ It doesn’t matter your figure or your budget. A few little basics, like a good black cashmere turtleneck, go a long way. Pair them with a pencil skirt, wide trousers, or skinny jeans. When you put in the effort, you look good, you feel good, and it shows.”

Inspired by Carr’s insights, I found myself revisiting my winter wardrobe. I looked at my trusty black puffer coat and saw potential with a bold scarf or bright gloves. My neglected brooches might finally get their time to shine.

Carr’s approach to winter fashion is refreshingly practical. In Chicago, we may not be able to wear our jackets unzipped and always follow the latest trends during these harsh winter months, but it’s not always about the trends. 

Then I remember what really helps me get through the winter season. I text my friends, plan a night out and, layered up with my giant gray coat, enjoy our conversations that keep me warm, no matter what I wear.