What to Wear for Winters in Chicago: Outfit Ideas That Bring the Heat

Chicago isn't for people who aren't brave. One day you are having coffee in the cold. The next, it's freezing with snow and a wind chill that makes you wish you had brought that thicker coat. Layering is important. That doesn't mean you can't be warm and look good this winter.

All you need to look good and feel comfortable is some streetwear. Think about these shoes, a soft sweatshirt, a bright jacket and any mix of items that layer well without being too thick. No matter where you are going in the city, whether downtown hanging out with your friends or just running your errands, this collection of clothes can have you ready.

Explore Tops and Bottoms to find streetwear, jackets, shoes and boots for every situation. Find out how to put together winter outfits and be stylish while staying warm and comfortable.

Dress for Chicago Weather, Not Just the Forecast

Winter in Chicago can be very unpredictable, so consider this when planning an outfit for the morning. The average high temperature for the city in January is approximately 32°, and the average low temperature is approximately 19°. Snow is pretty typical in the wintertime, so plan ahead!

Begin with layers you can modify all day. A T-shirt with a hoodie or long-sleeve shirt can be worn under a heavier coat and jeans, joggers or heavier pants finish the job. When it gets really cold, wear a warm hat and gloves.

When heading out for a while, wear shoes suited to the conditions instead of choosing only what looks good. This ensemble is ideal for days when you're out for a while and don't want to wish you had worn warmer clothes.

Winter Outfits for Men: Keep It Fresh and Functional

Men's winter streetwear is perfect for colder days when you just want to throw on some comfortable layers and your favorite pair of sneakers and outerwear. You don't need much to look stylish and on-trend. There are a few staple items that can take you from day to night.

1. Go Classic With a Puffer Jacket and Sneakers

When it gets colder, puffer jackets are a good place to start. Layer one over a hoodie with a pair of joggers or Jordan Craig jeans, then add your favorite pair of Nike or Jordan sneakers from the Air Force footwear category, such as men's white Air Force 1 sneakers.

If you have picked a jacket in a bright color, vibrant print or with bold detailing, leave everything else subdued and keep it simple. Try a neutral-colored hoodie, dark jeans and a Jordan Craig jacket for an effortless, eye-catching everyday look.

On colder days, pick a puffer jacket that has enough insulation to match the weather forecast. Make sure it also has enough space to fit a comfortable base layer underneath.

2. Build a Streetwear Look With Nike Tech Fleece

A Nike Tech Fleece Windrunner Tracksuit and coordinating joggers will provide a comfortable base for a chilly winter look. Wear a thicker jacket over the top when you're out and about and don't forget to put on your go-to sneakers.

Tops & Bottoms has a few style options for this look. Nike Tech Fleece is a full set that gives you a complete outfit all in one.

This is a great choice for trips and running around town as well as lounging on the weekend. Keep in mind that the fleece by itself might not be enough on the chilliest days, so have an outer layer ready to go.

Winter Outfits for Women: Layer Up Without Losing Your Style

The most stylish winter looks for women have room for your personality to come through without sacrificing warmth. Whether you want a relaxed look with a hoodie and sneakers or something more elegant with a long coat or want to turn a puffer into the focal point of your ensemble, it's here.

1. Pair a Puffer With Leggings and Sneakers

For a casual everyday style put on a pair of leggings, a long-sleeve top, and a hoodie. Layer a puffer jacket on top. Wear your favorite lifestyle sneakers, and you're good to go shopping, attending casual meetings or enjoying any day when you want to focus on comfort in Nike athletic clothes!

For a more streamlined look, keep the black leggings on and wear a combination of neutral pieces finishing with a hoodie for a complete streetwear look. A women's mackage coat can also work well for a stylish cold-weather outfit.

Check out the women's clothing and jacket selections at Tops & Bottoms to see if anything looks like it might work for you. In very cold weather make sure to wear thermal underwear or base layers underneath and dress appropriately for the weather.

2. Make a Long Coat the Center of Your Outfit

Looking for something a little more formal? Go with a long coat and jeans and add Timberland 6-inch boots. The longer top layer can make your outfit look more polished without losing style.

Neutral options: Black, gray, cream and brown are simple to mix and match but you can wear a more vibrant coat for a bit more attitude. Heavier base layers: It's comfortable to wear lighter base layers when you are in a warm room and layer up when you're outside.

A long coat is a good clothing choice, but it must be warm enough for the weather, too. A chic coat is not always warm enough when the wind is blowing.

Choose Footwear That Can Handle the Cold

You are not dressed until you have checked what lies beneath your feet. Summer sneakers can be worn on winter days if the ground stays dry and the temperature is mild, but they may not be suitable when it's icy or slushy outside.

Know When to Wear Sneakers and When to Choose Boots

These kicks go with anything and everything from jeans to joggers, hoodies and puffer jackets. Sneakers are definitely a go-to for street style on a day when the pavement isn't covered in slush. Don't forget that not all sneakers can handle rain and snow.

Tough weather demands warm winter shoes that offer protection from the cold and other elements. When you're walking through snow and slush, waterproof boots might be the right choice.

And don't forget your shoes. Salt and mud can be especially harsh on lighter tones and can build up fast. Clean the grime when you return home and consult your shoe-cleaning recommendations.

How to Build Stylish Winter Outfits With What You Own

You do not have to remove your entire style and purchase a closet full of new clothes every winter. Simply select several key items to get you through the season: a nice jacket, comfortable pants, a hoodie or sweater and footwear that is practical for your daily lifestyle. Mix and match layers and colors.

For example, a neutral puffer looks great with several hoodies and different pairs of jeans. Mix and match a coordinating tracksuit into separates and wear the matching set or create your own new looks. Wear your go-to sneakers with several outfits if the weather permits.

Think about how each of your winter clothes will fit into the rest of your closet. Choose layers that allow flexibility, outerwear that is appropriate for the weather you encounter, and colors that will not clash.

Looking to lighten the load of your mornings by making getting ready a little bit easier? Add a few staple pieces to your closet that you can mix and match with lots of different outfits!

Final Thoughts

The art of layering means selecting items suitable for the weather. Puffer jackets, hoodies, denim jeans, tracksuits and suitable footwear combine to create Chicago winter wear that keeps you comfortable.

Check out the jackets, clothing, sneakers and boots at Tops & Bottoms to add some pieces to your weekly lineup. With a few tops and a few bottoms, you can stick to your style while facing the fresh weather.

Frequently Asked Questions

1. What to wear during winter in Chicago?

Dress in layers; start with a warm base add a sweater or hoodie and a jacket. Choose pants and footwear that suit the temperature and conditions.

2. Are puffer jackets fine for Chicago winters?

Yes. The warmth you will get out of it depends on the insulation and how it's constructed, so just make sure to pick one that's designed for the temperature you expect to encounter.

3. What are some easy winter outfits for men?

A puffer jacket over a hoodie with jeans and sneakers or a Nike Tech Fleece set under a heavier coat when it's very cold.

4. How can women style sneakers in winter?

Pair sneakers with leggings or jeans, a sweater or hoodie, and a warm jacket. Choose sneakers for suitable conditions and switch to boots when sidewalks are snowy or icy.

5. Can I wear regular sneakers in Chicago during winter?

You can wear them on dry days, but regular sneakers may not offer enough traction, insulation, or moisture protection for snow and ice.

6. What footwear is best for snowy Chicago days?

Look for boots or other footwear with suitable traction, insulation and water resistance. Check the conditions before heading outside.

7. How do I make outfits look stylish without feeling bulky?

Use layers that fall comfortably, keep your outfit simple and choose an outer layer that leaves enough room to move without restricting you.

8. Which jackets work for winter streetwear?

Puffers, insulated parkas and heavier winter coats. Plus, varsity, bomber and leather jackets can work for milder days.