Chicago Winter Outfits: 14 Real Looks for Wind, Snow and City Days
14 real Chicago winter outfits from women who live there. Long puffers, faux fur, shearling and smart layers that keep you warm in the Windy City and still look cute.
Chicago winters are no joke. The wind off the lake makes 20 degrees feel like 5, and you still have to walk to the train, the office or dinner.
These 14 real Chicago winter outfits come from women who know that cold. For each look I share what it is, when to wear it, how to style it and who it works best for.
🎨 Colors that shine on a grey Chicago day
1. Shearling leather jacket with black layers
View this post on InstagramA post shared by @wearlikewow (@wearlikewow)
📸 Look by @wearlikewow
A black leather jacket with a thick cream shearling collar over all black basics. It is warm, a little edgy and great for city streets.
Wear it for a weekend in River North or drinks with friends. Zip it up when the wind picks up. Great for anyone who likes a cool girl look.
🛍️ Pieces to grab
- Shearling lined leather jacket
- Black turtleneck
- Black straight pants or jeans
2. Grey wool coat with tall boots
View this post on InstagramA post shared by @ilikeamy_ (@ilikeamy_)
📸 Look by @ilikeamy_
A long grey wool coat with black knee boots and a short skirt or shorts with tights. Classic and polished for a crisp day.
Wear it on a dry cold day for brunch or a museum. Add thick tights so your legs stay warm. Perfect for anyone who likes a ladylike look.
🛍️ Pieces to grab
- Long grey wool coat
- Black knee high boots
- Fleece lined tights
3. Black coat and mini skirt by the river
View this post on InstagramA post shared by @jacquieflorescu (@jacquieflorescu)
📸 Look by @jacquieflorescu
A long black coat over a grey mini skirt with black tall boots and a black beanie, posed along the Chicago River.
Wear it for a city walk or photos on the Riverwalk. Tuck a scarf inside your coat for extra warmth. Great for anyone who loves a sleek, all black base.
🛍️ Pieces to grab
- Long black coat
- Grey mini skirt
- Black beanie and tall boots
4. Short puffer with wide leg pants
View this post on InstagramA post shared by @nicolethang (@nicolethang)
📸 Look by @nicolethang
A cropped puffer jacket with dark wide leg pants and sneakers in the Loop. It is the kind of outfit that survives a 10 degree commute.
Wear it for work days with lots of walking. Add warm gloves and a beanie. Perfect for anyone who wants warmth first but still looks put together.
🛍️ Pieces to grab
- Cropped puffer jacket
- Dark wide leg pants
- Thick sneakers
5. Faux fur jacket with a black mini
View this post on InstagramA post shared by @misskren (@misskren)
📸 Look by @misskren
A fluffy brown faux fur jacket with a black mini skirt and black top against a brick wall. Glam and cozy at the same time.
Wear it to dinner or a night out in the West Loop. Go for opaque tights and boots. Great for anyone who loves a bit of glam.
🛍️ Pieces to grab
- Short faux fur jacket
- Black mini skirt
- Opaque black tights
6. Long white puffer with jeans in the snow
View this post on InstagramA post shared by @haileyalmsted (@haileyalmsted)
📸 Look by @haileyalmsted
A long white puffer coat with a black top, light jeans and white sneakers on a snowy day. Fresh, bright and very warm.
Wear it on a snowy weekend or for holiday photos. A long puffer covers your hips and thighs from the wind. Great for anyone who runs cold.
🛍️ Pieces to grab
- Long white puffer coat
- Light wash jeans
- Warm white sneakers or boots
7. Long black puffer for over 40
View this post on InstagramA post shared by @deborahsorlie (@deborahsorlie)
📸 Look by @deborahsorlie
A long black puffer coat with a white turtleneck and black pants. Simple, warm and so easy to wear every day.
Wear it for errands, school pick up or work. This is the one coat every Chicago woman needs. Perfect for women over 40 who want comfort and style.
🛍️ Pieces to grab
- Long black puffer coat
- White turtleneck
- Black leggings or pants
8. White faux fur coat with a fur hat
View this post on InstagramA post shared by @_reillyjohnson (@_reillyjohnson)
📸 Look by @_reillyjohnson
A big white faux fur coat with a matching fur hat by the river. It is a full winter wonderland look.
Wear it to a holiday event, a fancy dinner or photos downtown. Keep the rest of the outfit simple. Great for anyone who wants to make a statement.
🛍️ Pieces to grab
- White faux fur coat
- Faux fur hat
- Neutral knit dress or pants
9. Pink puffer with bows in the snow
View this post on InstagramA post shared by @kaykaybrown (@kaykaybrown)
📸 Look by @kaykaybrown
A soft pink puffer jacket with pink bows and a cozy hat in the snow. Sweet, warm and so fun.
Wear it for a snowy day out, sledding or a walk in the park. Pink brightens up grey winter days. Perfect for anyone who loves a girly look.
🛍️ Pieces to grab
- Pink puffer jacket
- Pink ear muffs or hat
- Matching mittens
10. Shearling jacket with jeans on a sunny day
View this post on InstagramA post shared by @ginnypaxkrosel (@ginnypaxkrosel)
📸 Look by @ginnypaxkrosel
A brown shearling jacket with light straight jeans on a rooftop under a blue Chicago sky.
Wear it on a sunny but cold weekend day. Shearling blocks the wind well. Great for anyone who likes a casual western vibe.
🛍️ Pieces to grab
- Brown shearling jacket
- Light straight jeans
- Brown ankle boots
11. Brown fur coat with a fur hat
View this post on InstagramA post shared by @chi_rhodesfashion (@chi_rhodesfashion)
📸 Look by @chi_rhodesfashion
A rich brown faux fur coat with a matching fur hat, a black turtleneck and dark sunglasses. Pure old Hollywood in the city.
Wear it for shopping on the Magnificent Mile or a nice lunch. Add a structured bag. Great for anyone who loves a luxe look.
🛍️ Pieces to grab
- Brown faux fur coat
- Faux fur hat
- Black turtleneck
12. Cream fur coat with a red dress and red boots
View this post on InstagramA post shared by @stylecadenza (@stylecadenza)
📸 Look by @stylecadenza
A cream faux fur coat over a red knit dress with red boots on a snowy bridge. Bold and festive.
Wear it to a holiday party or a December date night. Matching your dress and boots looks very chic. Perfect for anyone who loves color.
🛍️ Pieces to grab
- Cream faux fur coat
- Red knit dress
- Red knee boots
13. Burgundy faux fur coat with jeans
View this post on InstagramA post shared by @syl.img (@syl.img)
📸 Look by @syl.img
A burgundy faux fur coat with light jeans, a burgundy hat and a small tan bag. Proof that jeans and a coat can look special.
Wear it for a day of shopping or coffee with friends. Pick a coat in a rich color and keep the rest simple. Great for anyone who wants one easy wow piece.
🛍️ Pieces to grab
- Burgundy faux fur coat
- Light wash jeans
- Burgundy knit hat
14. Black coat for ice skating downtown
View this post on InstagramA post shared by @masonoglesby (@masonoglesby)
📸 Look by @masonoglesby
A black puffer with a black beanie and warm layers for ice skating at the park. Cozy and ready for fun.
Wear it for skating, a holiday market or a walk by the Bean. Layer a thermal under your sweater. Perfect for anyone with an active winter plan.
🛍️ Pieces to grab
- Black puffer jacket
- Black beanie
- Thermal top and leggings
Long puffer vs faux fur coat in Chicago
Both work in Chicago. Pick based on your day.
Long puffer
- Best for wind and snow
- Covers your legs
- Easy to wash
- Great for commutes and errands
Faux fur coat
- Best for nights out and events
- Looks very dressy
- Warm but shorter
- Great for dinners and photos
How to dress for Chicago wind and cold
The trick is layers and covering your skin. Wind finds every gap.
- Start with a thin thermal top and leggings
- Add a warm sweater or turtleneck
- Choose a coat that covers your hips or thighs
- Wear a hat that covers your ears
- Pick boots with grip for icy sidewalks
- Add gloves and a big scarf
💡 My tip
Buy a coat with a hood or wear a hat every day. Most of your heat leaves from your head, and the Chicago wind will remind you fast.
Quick guide
- Work commute: long puffer, wide pants, warm sneakers
- Night out: faux fur or shearling, mini and tights, heeled boots
- Snow day: long white or black puffer, jeans, snow boots
- Holiday event: fur coat, dress, matching boots
Chicago winter outfit FAQs
What do people wear in Chicago in winter?
Most people wear a long puffer or a warm wool coat, a hat, gloves, a scarf and boots with good grip.
How cold does Chicago get in winter?
Highs are often in the 20s and 30s Fahrenheit, and wind chill can make it feel below zero.
Can I wear jeans in Chicago winter?
Yes. Add fleece lined jeans or thin leggings under them, plus tall boots and a long coat.
What boots are best for Chicago winter?
Waterproof boots with a warm lining and good tread are best for snow, slush and salt.
Stay warm, look cute
Chicago winter outfits are all about smart layers, a great coat and good boots. Pick one look for work, one for weekends and one for nights out, and you are ready for anything the Windy City throws at you.
Planning more winter trips? See my NYC winter outfits, cold weather outfits, casual winter outfits for women and Europe winter outfits.
