What to Wear in Chicago?

What to Wear in Chicago? 2017-07-24T14:33:45+00:00

So you’re taking a trip and want to know what to wear in Chicago? Chicago is like most American cities and the dress code for the average Chicagoan, is well American! What’s the best way to describe it; the style is a little lazy and perhaps casual. From a personal observation it’s clear that, on average, Americans dress with looser clothing and easier style compared to our European counterparts. However there is also great style and ideas.

If coming to Chicago and want to know what you need to wear then continue reading. If you’re a tourist and want to know what the general Chicago look is, this post can help. This post is meant to help inspire on what to bring for your up-coming trip and get a general idea of the “look.” I want to note that I’m not going to cover every single style there is but rather focus on the average look and my recommendations.

What to Wear in Chicago?

Easy, Preppy, and Comfort are the 3 words that come to mind when thinking on the Chicago style. I wouldn’t say that the average Chicagoan is trying to look sexy but they are definitely aiming for comfort with a mix of American preppiness taken from the 40s and 50s. An average Chicagoan values comfort above style and wouldn’t think to buy a shoe that looked great but caused pain. The goal is to be comfortable first and stylish second.

Women wear all types of clothing depending on the season. Usually I see dark blue jeans, shorts, jogging outfits, t-shirts, dresses and sometimes skirts if it’s summer. It can be windy in Chicago, at least near the lake, so bring a jacket for any part of the year. Whatever you bring make sure the colors and pieces of clothing are uniform with other parts of your clothing! They all need to work together.

I see so many women who have too many colors mix matching with one another, that the outfit doesn’t look appealing. Stick with boots or at least shoes, try no tennis shoes! It can be said that many travelers wear tennis shoes and they are comfortable for walking but they aren’t fashionable. If you don’t want to wear a heel try flats, some type of boot, or riding boots.

There are some women who do put in the effort to make sure they look the part and I see plenty of colorful dresses, skirts, blouses, sometimes high-heels, and lots of jeans. The “hipster” or the “vintage” or what I call the Urban Outfitters look is popular. I see many girls go with looks from the 50’s, 60’s or 70’s, however I see many women who wear outfits from stores like H&M, Forever 21, Zara, and the many stores that line Michigan Ave. It’s the modern yet still casual cute look.

What to Wear in Chicago - A nice beginning of spring end of fall look

Men usually wear a plaid dress shirt for work, maybe some boots or tennis shoes, jacket or pea-coat if it’s cold, some type of hat or beanie, jeans and maybe a sweater. Sometimes I see scarves in the wintertime but surprisingly a lot of men don’t own one. I recommend bringing one. I wear a lot of fitted express shirts but the average male favors a looser fit. Chicago men like to wear chukka style boots, cardigans, sperrys, tennis shoes, and dress shirts. Dark jeans are also popular in both the summer and winter.

It’s interesting to note that there is a difference between how gay men dress compared to their straight counterparts. In the US its normal to see straight men wear looser clothing and jeans like boot cut, where as gay men like to wear more fitted clothing in every aspect.

Like the women, I have seen the “Urban Outfitters look” be very popular here. It’s the “vintage” look and many men my age wear it. However, many men also like to dress in the preppy 40’s to 50’s style, where men roll up their jeans neatly, wear some type of frames, dark jeans, a cardigan, with a button up dress shirt. This is VERY popular in Chicago at the moment and I have to say I do like the look.

Both men and women should buy at least one scarf. In the winter it’s almost essential to have a nice designed wool scarf as it will be stylish and keep you warm. Add a sleek black pea-coat to finish the outside look. Stick with dark jeans for the most part.

For the summer, my recommendation is to stick with a fitted t-shirt, plaid shirts, blouses, shorts, jeans, shoes and maybe some boots. Some people do wear dress pants but it’s mostly office workers. Remember it can be quite warm during the day but then cool off at night quickly.

Season to Season

Because Chicago has all 4 seasons, what you wear depends on what time of year you travel. In the winter and even as far as April and May most men and women wear combinations of jackets, sweaters, pea-coats, scarves, gloves, boots and jeans.

Winter is all about layering and staying warm so I wouldn’t worry about the colors since you will be bundled up with a dark jacket on top. I would think about buying some winter boots or maybe hiking boots when it’s snowing. The salted streets can ruin nice pairs of boots fast.

What to Wear in Chicago - Mens winter blue jacket look

Spring temperatures can swing from hot to cold quickly, so I would pack a combo of winter and summer clothes. Most men and women wear combos of shades of browns, blues, blacks, reds, greens and grays with perhaps a colorful scarf.

Sometimes you can wear shorts so I recommend packing those. T-shirts and a pair of jeans are popular among men and women and so are tennis shoes. However, I would recommend staying away from those unless you plan to workout or jog. Find neutral colors with a small amount of bright colors to add some depth to the outfit. Keep it form-fitting with a touch of American prepness.

Summer Style in Chicago

Summer, a range of outfits are seen, from as bad as sofie shorts and sweats to dress shirts to nice pants, dresses and dress shirts (mostly for the men and women who work downtown). It can be surprisingly warm in Chicago so my suggestion is to wear light-colored clothing, like light blues and whites. Stay away from black.

For pants it is acceptable to wear a pair of jeans, fitted t-shirts or blouses, and wear comfortable casual boots or shoes. Try to stay away from sandals and tennis shoes! Mix in some colors to your outfit through your handbag or add an accessory like a bracelet or watch. Think casual American preppiness for the ideal Chicago look.

In basic it’s best to keep it comfortable and easy to wear. I don’t recommend wearing any type of athletic wear or over-sized collegiate shirts or anything too flashy.

what to wear in chicago - Chicago comfortable style

Fall, the weather can be quite pleasant but sometimes it turns chilly. You’ll need to bring a jacket but there is a chance that during the day you won’t need it. Plaid is popular with mens dress shirts as well as colors like reds, blues, grays, and greens. Women wear dark jeans with a light jacket as well as light scarves. For both men and women, I would go with some sort of boots and maybe shoes like flats. Leather boots are actually quite popular with both men and women.

What to Wear in Chicago - Womens fall green jacket look

The Look

It’s sad to say that the average Chicago look is quite frumpy however there is definitely a revival of the old American classic preppy look. It’s very popular among men and women in their 20’s and 30’s. Both Chicago men and women value comfort and so looser clothing is more in style here. I do recommend that when buying clothing make sure it fits your body correctly and try to not have any sag in your clothes. Men love a more loose fit in their jeans compared to their European counterparts. Personally, I feel your jeans should be more tight-fitting but the looser look is popular.

Look Chicagoan?

I would search stores like

  • Zara
  • H&M
  • TopShop
  • Calvin Klein

  • Banana Republic
  • GAP
  • Macys
  • Express

  • Urban Outfitters
  • Nordstroms
  • Neiman Marcus
  • Ralph Lauren

to name a few. My recommendation is to stick with neutral to dark colors for things like t-shirts and pants and add the color with a scarf or with your shoes, especially in the winter. Compared to European men, American men do not favor the metro-sexual look so you may stand out if you like it. However there are a few men who really do know how to put a modern yet handsome look together.

As a whole Chicago is actually more stylish than most American cities and appreciation for good looks are still seen here.

Womens winter style in Chicago

My recommendation is to find clothing that fits nicely on your body and to bundle up during the winter. Most travelers come during the summer when the weather is a perfect temperature to wear dress shirts and jeans by day and then sometimes pop on a light jacket at night. For women it may be harder to wear high-heels all day so I recommend only at night when you go out. Shorts and jeans are acceptable for women as well as a stylish top.

In Basic

If traveling to Chicago and you want to blend in with the masses, stick with comfort and casual. Jeans and a t-shirt usually work. However my recommendation is to turn it up a notch and put a spin on that American Classic Vintage look. I would recommend some leather boots or high heels, skirts and dress, dress pants, a dress shirt, fitted blouse, and definitely a scarf. Scarves are a great add-on and will be necessary in the winter, fall and even spring.

what to wear in chicago - Man with hat and suit in Chicago

What to wear in Chicago? Basically keep your style fresh, easy going, modern or classic, and above all comfortable… it will keep your look timeless. Chicago is a no fuss kind of city so it isn’t surprising to me that peoples clothing reflect that.




images by: shawnvoyage, refinery 29, tres awesome, erin, chicagostreetstyle, teenvogue, refinery29, infashionchicago, pinterest, tresawesome