The Fall Trends Chicago Women Are Actually Wearing Right Now

Photo Credit:@ohmyletto

Every city has its own style code. New York leans on head-to-toe black, L.A. thrives on crop tops year-round, but Chicago? We’ve mastered the balance of cozy and chic — because when the weather flips from sunny to “is that lake-effect wind?” in an hour, your outfit has to work hard.

When I was out shopping the other day, I kept noticing the same looks on repeat. Not in a boring way, but in that “oh, this is the uniform right now” way. These are the pieces real women in Chicago are reaching for — practical, polished, and stylish enough to wear anywhere from brunch in Wicker Park to running errands downtown.

Here are the fall trends Chicago women are actually wearing right now.

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1. The Aritzia Fleece Jumpsuit Set

If you don’t already own one, chances are you’ve seen it everywhere. The Aritzia fleece jumpsuit set is basically the cozy-chic uniform this season. It’s comfortable enough to lounge in but looks elevated enough for a coffee run. Neutral shades dominate, though I have mine in green — because yes, it’s that good.

Aritzia

Cozy Sweatfleece Mega Cargo™ Sweatpant

$88

Aritzia

Cozy Sweatfleece Mega Zip Hoodie

$88

2. Baggy Jeans + Adidas Sambas

This combo is the casual cool-girl look right now. Baggy jeans paired with Adidas Sambas are everywhere — from college campuses to downtown shops. It’s laid-back, effortless, and the Chicago answer to looking trendy without looking like you’re trying too hard.

Women's Low Super Baggy Jean

Cotton On

$79.99

Handball Spezial Sneaker (Women)

adidas

$110.00

3. Leather Jackets Everywhere

Chicago women know the power of a good leather jacket. It’s the piece that works over dresses, layered with hoodies, or paired with denim. Practical for the wind, timeless for style, and always giving that slightly edgy vibe.

Sabina Faux Leather Jacket

MANGO

$99.99

Leather Shirt Jacket

Nordstrom

$329.00

4. Matching Legging Sets

Activewear as daywear isn’t going anywhere. Matching legging sets — think Aritzia, Alo, or Amazon finds — are being worn with sneakers and long coats, proving that comfort and style can definitely coexist. It’s the look that says, “Yes, I worked out… or maybe I didn’t. You’ll never know.”

Two Piece Cross Back Tank Top

$38.99

5. Crewnecks and Layered Cardigans

When it’s too chilly for just a tee but not quite coat weather, Chicago women are leaning into crewnecks and cardigans layered over simple basics. Paired with jeans or leggings and topped off with layered jewelry, it’s casual yet elevated — the kind of look that takes zero effort but reads polished.

Long Sleeve Shirt

$14.99

Bow Tie Front Cardigan Sweaters

$43.99

6. Oversized Blazers + Sneakers

Street style meets practicality with oversized blazers paired with sneakers. This combo is perfect for days when your schedule goes from work to dinner without time for an outfit change. It’s one of those looks that makes even a simple tee and jeans feel fashion-forward.

The Curator Relaxed Blazer

Open Edit

$169.00

Essential Double Breasted Blazer

Good American

$248.00

7. Long Coats Over Everything

Chicago fall and winter are all about outerwear, and long coats are the go-to. Tossed over leggings, denim, or matching sets, they instantly make any outfit look expensive. Bonus: they’re functional against the unpredictable temps.

Longline Wool & Silk Blend Coat

Eleventy

$2,595.00

Picarol Double Breasted Wool Blend Coat

MANGO

$249.99

8. Baseball Caps with Anything

Forget saving caps for workouts — in Chicago, baseball caps are being paired with leather jackets, coats, even skirts. It’s equal parts practical (wind control) and stylish (adds that effortless edge).

Salty Embroidered Everyday Hat

Dalix

$19.95

Chicago women aren’t chasing every runway trend; they’re wearing what works in real life — cozy fleece sets, baggy jeans with Sambas, leather jackets, and layered cardigans that make a simple outfit feel intentional. These looks are everywhere right now, and they prove that Chicago style is about being practical without sacrificing chic.

And if you’re still staring at your closet wondering how to make your outfits work harder, my 100+ Wardrobe Essentials Checklist.