JUST FOR MEN

Chicago has its own flair and could definitely be the capital of mid-west fashion. However,
it’s a modern city and travelers should mix in their own style in deciding what to wear in
Chicago. Chicago is a big city, after all, with many different forms, but coming as a traveler,
you can bring your own flair, which is stylish and comfortable to wear.

Below I have examples of some of the clothes I would consider and some links to broaden
your search. My general advice is always to bring clothes that are fitted to your body style
or else the look will not work. Bring clothes that are easy to wear and easy to mix and
match. Men in the United States need to step up their style, and I think with a little
guidance, most can dramatically improve.

SHIRTS

For male travelers, the most essential part of your outfit for what to wear in Chicago is
your shirt. I have laid out some styles and shirts that will be comfortable to travel with as
well as stylish. Chicago has all four seasons, and it’s so important to check the weather
before you go to Chicago. Being a resident of Chicago, mornings near the lake can always
be chilly, even in summer, and that winter can be downright freezing. The weather can
jump dramatically, even more than cities like New York, so definitely always have a jacket
nearby.

PANTS

If you’re touring at night or going to a nice restaurant or it’s a chilly day than pants are
needed. I would bring a pair of chino pants or at least jeans and then maybe one other
pair of pants. Obviously, you can wear jeans anytime, and it would, of course, be
acceptable. Just know that it can be hot and wearing jeans may be uncomfortable during
those times. Other times in autumn and spring they are a necessity so definitely bring a
pair when deciding what to wear in Chicago. Of course in winter you may have to wear
long underwear under your pants if you plan to be outside for long periods.
JUST FOR WOMEN

Women traveling should consider what types of patterns, colors, and styles in deciding
what to wear in Chicago. Chicago is one of those cities where seasons matter, and
temperatures can vary quite a lot. There are days even in the summer where daytime
temperatures can be hot while temperatures at night can be chilly. My suggestion is to
bring the right mix of travel gear for each season and never forget a stylish jacket.
Temperatures can fluctuate, and you never know if you may need to cover up.

Keep your style to you but also consider some of the suggestions I have below. I like a fresh
modern look that isn’t over the top and is also travel-friendly. Chicago is a very American
style in terms of dress, but there is definitely a sense of fashion with at least some of the
population.

SHIRTS

For women travelers, the most essential part of your outfit for what to wear in Chicago is
your shirt. Chicago has all four seasons, so it’s necessary to bring tops in the colder months
that can be layered and for the summer to bring shirts that are easy to wear. Spring and
autumn toss up on the weather, so make sure to check the weather before you travel.
Below I have laid out some examples of modern looks that would work well in Chicago.

PANTS / SKIRTS

Of course, pants and skirts would also work while traveling and jeans are pretty universal
in Chicago. This is a personal preference, so go with whatever makes you comfortable
walking around all day. I laid out some styles to help in deciding what to wear in Chicago
that would be easy to wear and get great reviews.