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Men’s Style and Fashion Guide to Look Good in Chicago

People in the urban Midwest are focused on staying warm. During the winter, the Windy City’s weather can get brutal, so it’s important to know how to layer and how to insulate. 
Luckily, Perk is here to offer advice on Chicago vacation outfits and men’s outfits in general for this beautiful city by Lake Michigan.


What is Chicago fashion? 

Chicago fashion is centered around dark colors and sharp silhouettes. The people of this city value their warmth, but they also know how to make thick coats and fleeces look fashionable. 


Layering in Chicago

If there’s one thing the Midwest is known for, it’s fluctuating weather. You might be freezing in the morning but ready to hit up the beach by 3pm, so you’ve got to know how to layer accordingly. 
One way to make layers work for your Chicago men’s fashion is by layering a t-shirt under a button-up, then placing a jacket or a coat on top. This will do enough to keep you warm, but you can take off plenty of layers should the temperature increase. 
If you’re headed to a business lunch, keep the jacket on. For happy hour, take off the jacket and leave the button-up. For relaxing at a friend’s house afterwards, chill out in your t-shirt


What is considered street style?

Chicago street style is anything that will catch the eye of passers-by - in a good way! People in the Windy City aren’t ultra-fancy all the time, but they know how to make casual looks appear fashionable


How do people dress in Chicago in early May? 

In early May, men’s clothing in Chicago can be fickle - because the weather is fickle. On the brink of summer, it’s hard to know what works best. But we’ll help you with this next section. 


Trench Coats in Chicago

Your outer layer in Chicago should be both trendy and functional, and trench coats are the top option. They’re great to sport between spring and summer because they protect you from the elements, but they’re not heavy enough to make you sweat. They also look great with slim fit chino pants - the perfect business casual outfit. 


What to wear in Chicago August 2023? 

Most people know Chicago for its frigid winters, but its summers can also be sweltering hot. In August, you’ll rely heavily on a casual t-shirt and shorts. 


Hats and Glasses in Chicago

The sun doesn’t shine in Chicago all the time but, when it does, you’ll get some relief with a cool pair of shades and a nice hat. These accessories make your Chicago street style come to life - whether you’re going for a casual look or something more high-class. 


How can a man be stylish at 40?

Style doesn’t have an age limit. As long as you use your men’s style guide to your advantage, you’ll be just as stylish at 40 as you were at 30 and at 20. 


Tracksuits in Chicago

Windbreakers and tracksuits are all the rage in Chicago, especially if you break the outfit up and wear a simple bomber jacket or a pair of track pants. 


What should I pack for a weekend trip to Chicago? 

Your Chicago packing list should be things that make you feel comfortable. It’s a walking city, so be sure to pack shoes that you can move around in - just make sure they look good, too! 


Chicago Shoes

Popular summer shoes include loafers, boat shoes, bucks, and mocks. These are tough shoes that can handle the city sidewalks, but they also look good with almost any outfit. 


What to wear in Chicago summer 2023?

If you’re looking for shoes to wear in the summer, look no further than desert boots. These boots are breathable and can be worn with or without socks which makes them perfect for the warmer months in the city. They look good with chinos, shorts, or jeans - the options are limitless. 


How do you dress like you’re from Chicago?

If there’s one thing that men’s clothing Chicago has, it’s confidence. As long as you feel good in what you’re wearing, you won’t stick out like a tourist. 


Chicago Blazers

Blazers are a great way to make your Chicago men’s fashion come to life. There are tons of styles to choose from and they can elevate your look to a whole new level. 


How should a 45-year-old man dress? 

No matter your age, it’s important to keep things interesting - and to do so in style. The main key, as a middle-aged man, is to find clothes that fit well.


Perk’s Philosophy 

What clothes are attractive on a guy?

We believe that, whether you’re in Chicago or someplace else, you’ll always look attractive when you’re wearing something that makes you feel good. For more men’s fashion advice from Perk, check out our blog