Winter style in Chicago often calls for functionality over fashion. As wind gusts hit 40 mph and ice freezes over Lake Michigan, there’s nothing that seems more appealing than bundling up in a mountain of warmth, no matter how frumpy the look may be. But in a city as vibrant as Chicago, where not even the cold weather stops residents from hitting the town with friends and loved ones, it’s imperative to have some kind of fashion sense under one’s belt. 

Whether you’re a Chicagoan looking to impress for an upcoming date night, a night out on the town, or you’re someone just looking for day-to-day guidance on “serving looks,” here’s what three of the city’s fiercest fashion experts in the stylish neighborhood of Gold Coast have to say about dressing for winter in the Windy City.

Mira Couture

Julie Mersine Romeli, fashion designer and owner of bridal shop Mira Couture (70 East Walton Street), has a lot to say about the versatility of Chicago fashion. “One of the perks of living in an all-season climate is the excuse to have an all-season wardrobe!” she told Chicago Star. “I get so excited when the weather turns, so I can break out a collection of clothes that haven't been in rotation for almost a full year! For winter, it's those chunky-heeled, fur-trimmed boots, and my favorite: a cable-knit, turtleneck, oversized, thick wool sweater!” 

The sentiment of feeling like one has a completely new wardrobe when the temperature dips is all too familiar. Clothes that have sat in storage for six to eight months can give fashionistas a fresh thrill without the need to spend additional money for new pieces.   

Layering and accessorizing for winter

The challenge, though, for dressing warm in winter can often be the fluctuation of cold-to-hot temperatures as people retreat indoors to the blasting heat, requiring the need to shed layers before breaking out in a sweat. 

“Winter dressing is more complex because you must ensure your outfit is cohesive indoors, and works just as well for the outdoor winter tundra winds,” Julie adds. 

While layering can be an adjustment, it can also provide an exciting chance to accessorize. 

“For formal occasions, winter provides an opportunity for more accessories, such as long satin gloves, capes and capelets, or a stunning silk neck scarf,” Julie says. “The winter season gives women the opportunity to embrace styles with long sleeves or a dramatic off-the-shoulder swoop of fabric, which benefits women who prefer more arm coverage. Accessories not only enhance the overall style but also offer a chance to show off multiple looks, as you can remove pieces as the evening progresses.”

NINA

Nina Mariano, boutique owner of NINA (110 East Delaware Place), takes a slightly different approach to slaying winter fashion in Chicago, starting from the bottom with an important staple of style: shoes. 

Put your best foot forward with fashionable footwear

“As a native Chicagoan, I learned early on that winter is no excuse to sacrifice style,” Nina said to Chicago Star in an interview. “To maintain my vibe in these times, I focus on footwear first. If there’s snow on the ground, you won’t catch me in heels or impractical shoes. I’m planning my entire outfit around a lug sole boot (Prada and Chanel are perennial faves). To offset the chunky shoe, I go for a high-style trouser, real leather pants or unique denim.”

While the occasional heel may be appropriate for select winter outings—especially ones where an Uber can take you straight to the door of your venue without sacrificing warmth—stylish boots are absolutely essential for getting through Chicago winters as an everyday choice. 

Using form-fitting pieces to feel your best 

When it comes to the outfit itself, Nina prefers a more form-fitting approach as opposed to an oversized sweater look. “I’ve always loved structured blazers (long and sleek, or cropped and boxy) and nothing feels chicer than a form-fitting black turtle neck underpinning. Pile on a few coveted accessories (think chains, charms, pendants, or a vintage brooch), and you’re good to go.”

And, of course, the most critical staple of winter fashion is outerwear, something Nina advises Chicagoans to prioritize functionality for, while leaving the fun for what’s underneath.

“The icing on the polar freeze cake of winter should always be a roomy, on-trend coat with a hood that will fit comfortably over everything. My current obsession is the Aritzia Super Puff in any length. While I’m usually one to show up in a statement coat, Chicago winters are not the time to showcase your favorite outerwear. Check your Puff at the door and carry on in your curated layered essentials from NINA.”

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Lafayette 148 New York

Michelle Kungis, store manager of Lafayette 148 New York (33 East Oak Street), discusses a unique international approach to styling for winter in Chicago. 

“For our winter collection, our creative director Emily Smith took inspiration from a trip to Tromso, Norway, in search of the Aurora Borealis,” Michelle told Chicago Star. “She watched the chromatic Northern Lights dance across the endless night sky, saw the icy shine of the Arctic, and experienced the comforting coziness of the Scandinavian culture. This served as the starting point as she set about translating the mysticism of the Northern Lights. The Scandinavian culture in Norway embraces hygge. It means a feeling of coziness and things that make you feel a bit more joyful. So, imagine sitting by a cozy fire, drinking your favorite drink in a cozy sweater with your cashmere socks on, feeling cozy.”

Chicago fashion goes Scandinavian

This fashion inspiration from Scandinavian culture makes total sense, as Swedish supermodel Elsa Hosk immediately comes to mind for her effortlessly cool, chic looks. Even in winter, while an occasional fun cheetah print might come into play for her style, Elsa stuns in matching outerwear and accessories of both leathers and warm wools.

“We show a versatile range of cross-seasonal looks, from cozy, tactile winterwear like fair aisle sweaters with matching hats and scarves,” Michelle said. “The journey goes from snowy escapism to city cocktail dressing. We have all nappa leather shirt jackets from Italy, as well as cashmere pants and reversible shearling coats.”

Neutral colors win Windy City style

While some might argue that a pop of color is what’s needed every now and then to get through the dreariness of a grey Chicago winter, there’s nothing quite like the chicness of a neutral, warm tone, particularly the iconic camel-colored wool trench coat that the most stylish women in the city seem to be sporting everywhere. 

At least that’s what I noticed upon first moving to the Windy City in the fall of 2022, shortly before purchasing my own from Mango—a simple but elegant winter staple I still get compliments on years later. 

Michelle went on to add, “As a native of Chicago, I personally remember calling my friends on a heavy snow day and doing a pub crawl or meeting at a cozy restaurant with a roaring fire. Lean into the cold, slip into your coziest knit, and keep moving in style!!!!”

Perhaps the key to truly winning Chicago style this winter is simply to remember to get out and about and explore all the city has to offer, because at least then you’ll have a reason to dress up at all.