Dressing Tips for Travellers: What to Wear in Chicago?

So, your next trip destination is Chicago! Great choice! Do you want to discover the secrets of street fashion in Chicago? Don’t worry about the fashion specific! Chicagoans wear the same clothes as the rest of Americans. This is a lazy and over-size style with enough space to implement the craziest ideas you have in your head into your look. There are no more than three words to give a characteristic to way of dress in Chicago. They are Easy, Comfortable and Preppy. Follow these words to be up-to-date. It is important to know that typical Chicagoans would never wear modern shoes if they are not comfortable to walk in.

Banana Republic Mall Location, 2/2015, by Mike Mozart of TheToyChannel and JeepersMedia on YouTube #Banana #Republic


Women Style

Chicagoan women pick clothes depending on the weather outside. There are no limitations for local women. The most popular items you can meet here and there on the street are jeans or shorts, T-shirts or oversized dresses, blouses if it is warm. The weather is changeable as everywhere in America, so, the jacket of all colors, length and texture can be very helpful. Honestly, jacket is good any season in Chicago. You can take all clothes you like but it would be great if all your clothes pieces can be easily moxed to make a new look.

What about the footwear? The rule is only one – no tennis shoes! You may wear sport or leather boots, shoes, high boots. If you want to look like locals, try to wear converses or sandals instead of tennis wear of your feet. High heels are not the best variant for travelling. If you want to look elegant but comfortable, you can wear flats or vintage boots.

Vintage style is always up to date. What does it mean? Just go out the street and look around. You can see girls dressed in old fashioned colored skirts, light dresses with jeans jackets and funky accessories. The vintage style is also called the hipster or Urban Outfitters. There is a charm to look like a girl model from the 50’s, 60’s or 70’s. Nevertheless, if you don’t like funky clothes, you can go around the city and buy something modern from H&M, Zara, Forever 21 at Michigan Ave. This is the popular place for shopping here. You can use car rental Chicago O’hare under 25 to rent a car and add your look with a vintage vehicle or modern powerful machine. Chicagoans don’t like going on foot around the city.



Men Style

Men’s style is not interesting or unusual. Typical Chicagoans like jeans with T-shirts or sweater and jacket. There is one thing, typical for American men. You should wear a scarf in cold. Chicagoans wear chukka boots, colored cardigans. The dark jeans are popular even in summer. Don’t wear fitted clothes if you are not gay man. Americans prefer oversized or sized but not fitted jeans, shirts and jackets.

Urban Outfitters - Temple Bar (Dublin)


Wear from Season to Season

Traditionally, Chicagoans love their changeable weather. They have all 4 seasons. What clothes you pick for today much depends on what weather is outside. The weather is cool and rather cold in winter and beginning of spring, including April. This is the favorable season to combine jackets, cardigans, scarves, gloves, black jeans and high leather boots. Winter likes layered clothes. You can start layer yourself from the colored T-shirt, blouse, jacket and maxi coat on the top. The long spicy scarf is also good. The high boots are good for snow. Try to pick hiking boots with a high rubber platform to feel safe on a slippery street.

Spring comes with warm temperature. The weather is rather changeable this season. Again, layered clothes are what you need. You can take you jacket off it the sum comes. Local men and women decorate their spring look with colorful scarves and hair. Jeans and T-shirt are probably the most popular clothes for male and female citizens. When it is hot, you can take off your jeans and put the shorts on. They are also good with the high boots and jeans jacket. Spring likes neutral colors with bright accessories. Try something green, red and orange.

Summer style needs wearing light or jeans shorts, skirts, dress pants, and dress skirts. The weather in summer can be unexpectedly warm in Chicago. That’s why pick the clothes of light materials and light colors. Stripped clothes and blue and white or black and white are in trend. Stay away from black. It is too hot for summer.

Fall is pleasant at the beginning and rather cool at the end of the season. It can be windy. Don’t forget your sweater or jacket. You may not need it during the day but it is better to have it somewhere in your bag. Women like wearing black or dark jeans with light or colored jackets and light scarves. The boots or shoes are different colors and styles. Vintage boots are popular for women and even for men in fall. Do you like high heels? High heels are popular on the street only in fall with the long sleeved cardigan and elegant scarf.

Lady cycle


Want to Look like Chicagoans?

Everything is simple. If you want to look like locals, you should drive your car to the local shops. The most popular brands you can meet are:

Top Shop, Zara, H&M, Calvin Klein, Urban Outfitters, Macy’s, Banana Republic, Nordstroms, Marcus Neiman, Lauren and others.

The style to dress in America is simple and rather classic. Try to pick natural colors for your pants, skirts or dresses and add some colors and forms for accessories. If it is winter, you can wear crazy colored hats, gloves or glasses. The mean style needs to be relaxed but modern in details. You shouldn’t look sexy. It is better to be crazy. One way or another, Chicago is considered to be the most stylish city in whole America. You can meet a lot of interesting looks and combinations in the streets. You cannot take everything you have in the wardrobe with you but you still can combine clothes details to look modern and comfortable.