Press "Enter" to skip to content

Chicago Men’s Style and Fashion Guide

Chicago, the third biggest city in the country, also has some of the wildest weather. While it certainly does make living in the city exciting, it also provides a recurring dilemma to its residents: “What am I going to wear today?” With spring here, the weather is going to be more random than ever. Spring-time in Chicago can be survived with your dignity intact, and without any fashion-induced rage.  Just make sure to follow these fashion-dos, and you will manage.


In Chicago, with such fluctuating weather, layers can be a man’s greatest ally. The fact is, there are so many things you can do to your appearance by utilizing layers properly (while staying true to your personal style), making them a helpful and essential tool. For example, wearing a T-shirt underneath a long-sleeve button up (with a jacket or coat on top) provides enough layers to keep yourself warm in the cold, but also provides versatility in that you can take off each of your layers depending on the weather. Some men also like to wear a nice scarf, or even a tie, to top off their look with some flair.

One of the best parts of sporting layers is that you can adapt to different social scenarios using the same outfit as well, just by switching out items depending on the situation.  Use the coat for more formal settings, take it off when you need to look trendy, and then just use the T-Shirt when you want to relax.

Some of the best places to find upscale jackets and shirts to layer are custom shops like Balani Custom Clothiers  or quality all-American guy stores like Haberdash.

Hats and Glasses

While there may not be as much sunny days in Chicago as we would like, there is no doubt that a nice hat or pair of glasses can act as great enhancers to already great clothes.  You do not need to wait for the sun to come out; glasses and hats are good ways to accessorize and make a statement about yourself, regardless of the weather.

mens fashion

Picking the right glasses to wear for your face can be tricky, though. First, you need to find out how your face is shaped. This is important, because the type of frame and lens which look best is dependent on this. When you find out what kind of frame compliments your type, try on many different pairs, getting a feel for which one makes you feel best (and matches the clothes that you normally wear.) As for color, your frames should bring out the best features in your face. If you cannot decide on a color, black and tortoise are great colors that look good with nearly any face tone. As for the frame styles themselves, if you’re not sure on what to get, Aviators and Wayfarers are classics that work well with mostly anybody. Try to find something that speaks to you.

Hats are a different matter. While it is encouraged to pick up a pair of classic-looking glasses, classic hats like the fedora have become a stereotypical wear. No matter how bad you are itching to put one on, don’t. Unless you’re a modern-day Sinatra, you probably aren’t going to achieve the effect you are looking for. Instead, op


t for a knit hat, a stylish (and classy looking) cap, or maybe even a nice baseball cap. The bottom line is: Don’t be pretentious.


In the Spring, it’s best to wear casual shoes. These are great, because they’re a step up from sneakers, but not as fancy, pricey or uncomfortable as dress shoes. Some of the most common types of these shoes are loafers, boat shoes, bucks, and mocks. The main benefit of this kind of shoe is that, considering the price, they work well with nearly any garment you have. Casual shoes are also comfortable, while being tough for street wear, and oftentimes re-sole able.

Living in an area with crazy weather like Chicago can keep things interesting, but it also means you have to constantly adapt to the new changes. That doesn’t mean you can’t do it in style. You can survive the spring, and you can look good doing it, while leading a stress- (and fedora) free life.

Be First to Comment

Leave a Reply

Your email address will not be published. Required fields are marked *