Chicago style - how do people dress there?

kuk416

O.G.
May 3, 2007
258
4
I will be visiting Chicago the first week in December and I was wondering what sort of styles are popular there? I am coming from CA where it never gets THAT cold. Also, what do people wear when going out at night? Like to bars or nice restaurants? Thanks!
 
Bundle up. Chicago is freezing in the winter. I have lived there before. It's also far less fashionable than NY. You can wear nice jeans to most places, even to some nice restaurants (not to Trotter's or anything, but to a lot). Just don't wear stone washed jeans or hairspray, or people will think you're from the suburbs, which is still common gear in some of them :smile:
 
I've lived there too and it's certainly one of the more stylish towns in the Midwest. Coming from California, you'll probably be chilly - and it gets pretty windy downtown near the lake. So bring a warm coat and a scarf.

For going out to dinner or hitting the bars, denim is fine. A killer top and great heels (strappy sandals would probably be too chilly) would look great! If you're sticking to the Gold Coast then you could get much fancier and no one would give you a second glance. have fun!
 
i also recommend bundling up. i am from CA too, and went to chicago for a training for work in January. In CA, I always wear open toed shoes to go out to the clubs at night. I only brought open toed shoes for going out at night in Chicago, thinking that even if it was cold it wouldn't be that bad. That was the biggest mistake ever!! I only had to walk a few blocks, and I was miserable. And people on the street laughed at me and said "I like your snow shoes!" It SUCKED!
 
You know, it's weird...definitely buy warm clothes in general, but the seasons aren't as predictable anymore...anyone from Chicago will remember last year how it was so warm on New Years Eve. It felt like fall! And you'll want to get one or two nice rain coats, you'll use them a lot. And I've seen a lot more women wearing dresses where I go now...*shrugs* different strokes for different folks. And I agree with FanAddict, the general neighborhoods all have pretty distinct styles. Any idea where abouts you'll be moving? And welcome! Chi's a really great town, you don't have to look hard at all to find things to do.
 
I go to Chicago a couple times a year. Last december it was SO warm when I was there. Usually it's freezing though. Just make sure you have a warm coat, hat, scarf and gloves. It gets so cold there that it really doesn't matter how you look as long as you're warm!

When I go out in the city, the places I go to are more preppy than fancy. I usually wear jeans or black pants, a cute cashmere sweater, pointy boots, fab bag and accessories, hair/makeup done (but not overdone). I feel like I blend right in.

Overall, Chicago has a more wholesome look than LA or New York. People aren't necessarily less stylish, but they're more conservative and covered up...
 
Overall, Chicago has a more wholesome look than LA or New York. People aren't necessarily less stylish, but they're more conservative and covered up...
You've hit the nail on the head! I was born and raised in Chicago but have lived in San Francisco for the past 10 years. Personally I don't think Chicago is any less stylish than NYC. Just like NYC, Chicago has "couture" neighborhoods as well as Irish bar n' jeans neighborhoods. I think of the stylish 'hoods of NYC as being very "Sex and the City," whereas in Chicago, the most stylish areas are more Chloe or Chanel-ish...elegant and upscale but not as overtly haute couture and experimental as NYC.

For evenings out, dress like you would in CA....in layers! For bars, wear a halter top under a warm and fuzzy shrug, skinny jeans tucked into stiletto knee boots, and a cropped wool coat over that. It will be toasty inside the bar so you won't have to wear a super-thick sweater.

For fancy restaurants, wear a dress with opaque tights and ankle boots. Or, a sexy silk blouse with black trousers and closed-toe pumps. Of course, how dressy you get totally depends on where you're going. :smile:

Chicago also offers the opportunity to accessorize in fun ways: wool hats, scarves, etc. You will have a GREAT time! Chicago is such a fun and festive place, especially during the holidays!
 
I've lived in Chicago my entire life, and the first week of December isn't that bad. It's usually at least in the 30's or 40's, which to us, is not totally freezing yet. I would at least have a wool coat, scarf and gloves though. Like others have said up top, the styles vary from neighborhood to neighborhood.
 
You know, it's weird...definitely buy warm clothes in general, but the seasons aren't as predictable anymore...anyone from Chicago will remember last year how it was so warm on New Years Eve. It felt like fall! And you'll want to get one or two nice rain coats, you'll use them a lot. And I've seen a lot more women wearing dresses where I go now...*shrugs* different strokes for different folks. And I agree with FanAddict, the general neighborhoods all have pretty distinct styles. Any idea where abouts you'll be moving? And welcome! Chi's a really great town, you don't have to look hard at all to find things to do.

I'm just visiting Chicago for vacation - I have never been, but I'm really looking forward to it. I've heard it's a fantastic city!
 
Bundle up. Chicago is freezing in the winter. I have lived there before. It's also far less fashionable than NY. You can wear nice jeans to most places, even to some nice restaurants (not to Trotter's or anything, but to a lot). Just don't wear stone washed jeans or hairspray, or people will think you're from the suburbs, which is still common gear in some of them :smile:

Do you think it's ok to wear jeans to Chicago Chop House? That is one of the places we will be having dinner. In California, you can wear jeans everywhere, but I don't mind dressing up a bit. In fact, I get tired of wearing jeans EVERYWHERE.
 
Also, what do guys tend to wear? I'm so used to seeing the striped button down shirt and jeans look, but is it different in Chicago? Would slacks at a nice restaurant or bar be more appropriate? Or are jeans ok for men, too (easier to pack).