15 Ways Fashion People In Chicago Are Wearing Jeans this Winter

Photo Credit:@lwethu_mcusi

Winter is my least favorite season to get dressed. I mean, living in Chicago, who’s really seeing my outfit if I’m wrapped in a gigantic coat just to keep warm? I digress. But I don’t dress for the male gaze I dress because I love the way I feel when I look put together. Even on work-from-home days, I’ll reach for a soft pair of jeans that feel more like sweatpants.

Lately, I’ve been experimenting with new outfit formulas to bring a little spark back into this cloudy winter weather. If your denim rotation could use the same boost, consider this your cheat sheet for jeans that actually feel worth getting dressed for.

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1. The Classic: Long Coat + Straight-Leg Jeans

Nothing looks more effortlessly pulled together than a wool coat draped over straight-leg jeans. It’s that quiet luxury moment — the kind where you could be running errands or meeting someone for coffee, and no one would know the difference. Bonus: it keeps you warm without swallowing your shape.

Walmart

Oversized Faux Wool Coat

$59.00

Walmart

High Rise Straight Jeans

$27.00

2. The “I Tried” Trick: Monochrome Denim

When in doubt, go tonal. Matching your jeans to your sweater or coat instantly reads intentional — even if you were rushing five minutes ago. Shades of cream or gray feel especially chic in winter light.

Walmart

Patterned Mock Neck Sweater

$26.00

Walmart

Plus Relaxed Low Slung Jeans

$28.00

3. The Cozy Combo: Oversized Sweater + Loafers

An oversized knit half-tucked into jeans says, “I’m comfortable, but I didn’t give up.” Add loafers or lug-sole boots and suddenly, you’re the main character at your local coffee shop.

Walmart

Long Knitted Open Front Oversized Color Block Outerwear Sweater

$59.99

Walmart

Faux Leather Loafers with Buckles

$24.98

4. The Texture Play: Shearling or Faux Fur

Winter style is all about texture. A cropped shearling jacket or faux-fur coat against denim adds instant dimension (and warmth). Even better if your accessories — think gloves or bag — pick up the same texture.

Walmart

Faux Fur Coat

$39.99

5. The Power Move: Blazer + Scarf

Swap your puffer for a structured blazer layered with a thick scarf. It’s giving “I have meetings, but make it fashion.” A pair of heeled boots or slingbacks completes the look without trying too hard.

Walmart

Scrunch Sleeve Crepe Blazer

$38.00

Walmart

Soft Knit Long Thick Scarves

$12.99

6. The Chic Layer: Button-Up Under a Sweater

This combo is a cold-weather secret weapon. That crisp collar peeking out adds polish, and you can play with proportions — cropped knits, longer shirts, whatever flatters your shape.

Walmart

Oversized Cable Knit Sweater

$36.99

7. The Weekend Uniform: Puffer + Beanie

You can’t talk winter in Chicago without mentioning puffers. Keep it streamlined with ankle-length jeans and sneakers or waterproof Chelsea boots. Add a beanie that actually matches (trust me, it makes a difference).

Amazon

Long Sleeve Zip Puffer Jacket

$69.99

Amazon

Chelsea Boots Slip on Chunky Heel

$39.9

8. The “Girls’ Night” Denim

Dark-wash jeans, a statement top, and a bold earring — it’s the easiest formula for looking done-up without being overdressed. If your outfit feels too simple, add a red lip or sleek hair part.

Amazon

Textured Basic Knit T Shirt

$24.99

Amazon

Wide Cuff Jeans

$39.58

9. The Layered Look: Denim on Denim

The Canadian tuxedo has officially rebranded. Think different washes, fitted silhouettes, and a statement belt to break it up. If you’re feeling bold, add a colored coat on top for contrast.

Amazon

Denim Tie Front Top

$39.99

Amazon

Ribcage Straight Ankle Jeans

$98.00

10. The “School Pickup Chic” Combo

Matching knit set (or hoodie + tailored coat) with jeans and sneakers. Effortless, cozy, and practical — which is the holy trinity of winter fashion.

Amazon

Warm Double Breasted Wool Pea Coat

$65.99

Amazon

Levi's Womens 724 High Rise Straight Jeans

$69.50

11. The Luxe Add-On: Statement Belt

Belts are the easiest way to make jeans look designer. Try a wide leather belt with an interesting buckle over a tucked-in turtleneck. It’s small, but it changes everything.

Amazon

Leather Belt Studded

$16.97

Amazon

3 Pack Womens Mock Turtleneck

$33.99

Amazon

Wide Leg Jeans High Waisted Stretchy Cuffed Baggy Denim Pants

$32.99

12. The Flare Moment

Flare jeans elongate the legs and balance winter layers beautifully. Pair with platform boots or pointed-toe heels and a cropped jacket. It’s giving ‘70s sophistication — no disco ball needed.

Amazon

Sherpa Moto Leather

$55.99

Amazon

Baggy Stretchy Jeans

$37.99

Amazon

Ankle Boots for Women

$54.99

13. The “Unexpected Pop”

Add one piece that feels slightly out of place — a satin blouse, a sparkly clutch, or even a bright-colored coat. It gives your denim that editorial twist that looks intentional (even when it’s just good instinct).

Amazon Essentials

Women's Top Handle Handbag

$30.40

14. The Minimalist Trick

Stick to three pieces: jeans, a great sweater, and standout shoes. The key is proportion — slightly slouchy denim, structured knit, sculptural footwear. When done right, it’s the quietest flex in fashion.

Amazon

Trendy Mock Neck Fringe Tops

$29.98

Amazon

High Waisted Wide Straight Leg Stretchy Baggy Jeans

$39.99

Amazon

Square Toe Chunky Heeled Boots

$74.99

15. The “Date Night, But Chill” Outfit

Straight-leg jeans, fitted long-sleeve top, trench or long wool coat, and kitten heels. Simple, flattering, and surprisingly romantic — no sequins required.

Amazon

Cotton Long Sleeve Mock Turtleneck Tops

$39.99

Amazon

Levi's Womens 724 High Rise Straight Jeans

$69.50

Amazon

Closed Toe Dressy Bow Heel

$54.99