8 Rules for Cold, Bold Chicago Fashion

If there are two words to describe Chicago, they’re cold and bold.

Chicago might not be known for its fashion. But during the year I lived in that city, I had learned that people were always bold. Bold attitudes, bold fashion statements, bold choices.

The best way to ensure you’re pulling off the essence of Chicago culture: be bold, be comfortable, be brave. There will be times where you’d freeze your ass off but you can still look good doing it.

With a little help from singer and Chicago native Grace Kinter, we put together eight rules for Chicago style.

Photography by Broderick Baumann


1. Don’t be afraid of a turtleneck.

It’s nerdy but you need it. That being said, you can get away with fashionable nerdy looks! Or for days where you want attention on your legs. Or when you want to experiment from your usual fashion vibe. Either way, it’s an essential basic piece to keep in your wardrobe.

2. Have one eye-catching piece.

Make sure your look isn’t head to toe black unless that’s what you want. Stay away from having too many eye-catching pieces, you might end up looking like a blob of distractions. Have something that you want to keep as your focus, everything else should easily coordinate with your focus piece.

3. Fur is your friend.

You don’t have to kill any animals or blow your paycheck on a fur coat, it can be faux! Thanks to celebs like Rihanna, Kendall, and Bella Hadid, fur coats are making a comeback. And you can make it part of your wardrobe as well, as long as you know how to match it with the rest of your attire. As long as you’re pulling it off,  you can have fun with fur coats in terms of color; pink, red, green, white, etc.

4. Make sure your shoes are functional.

If you’re gonna have the balls to wear heels, at least make ’em comfortable, or avoid that and just wear sensible shoes. Shoes can even be used to be your focus point BUT remember: be bold, be comfortable, and be brave. If your shoes don’t match 2 out of the 3, perhaps they’re not your best option.

5.  Accessorize to amplify, not clash.

What you add to make your look pop is up to you, but keep it relative to the rest of what you’re wearing. Accessories have the power to embrace your look or flunk it. Sometimes you don’t even need multiple items to accessorize, it could be that perfect pair of earrings that completes it, or that purse in your closet that brings it all together, or maybe that really cool hat in your closet. Know when to add and when to subtract.

6. Don’t be afraid to mix styles.

If you have one specific style you were going for, keep in mind that its ok to add something that can contrast it. Grace usually likes to keep the idea of urban-wear in her style.

“Even if I’m going with a more bohemian or beach look,” she said, “I try to throw in something to throw it off a little, like a camo jean jacket with a nice black dress or something. So don’t be afraid to mismatch or mix up patterns and colors.”

7. Check your weather app before you leave the house.

Chicago is called the windy city for a reason, you don’t want to be the chick wearing a super short skirt flashing everyone and their grandma. Or that one girl wearing shorts on a negative 10-degree day because she clearly didn’t check her weather app. Dress with the weather in mind; you can still wear a short skirt but pair it with modest tights or a long jacket to protect your derriere from exposure.

8. Vintage shopping is your friend.

The youngsters mostly stick to unique and vintage pieces that always left you with the question, “Where did you get that?” They always said the thrift store.

Chicago is FILLED with trendy and urban-style boutiques and shops. You just gotta know where to look. Some places would have specials like “all you can fit into your black bag: $1” and it would literally be whatever the heck you can get into that bag. Other thrift stores were unreasonably priced, like a vintage Tommy Hilfiger tank top for $47. Only you can decide if that’s worth it, but the important thing is it’s there.

Check out these places.

Buffalo Exchange, Wicker Park

1478 N Milwaukee Ave, Chicago, IL 60622

The Ark Thrift Shop

1302 N Milwaukee Ave, Chicago, IL 60622

Urban Outfitters Surplus Store

2352 N Clark St, Chicago, IL 60614

Good Will,Near West Side, West Loop

1201 W Washington Blvd Chicago, IL 60607


22 N State St, Chicago, IL 60605

840 N Michigan Ave, Chicago, IL


107 S State St, Chicago IL, 60603

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