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.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 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.
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