Heading to Chicago and Cleveland next week. Any spots I should check out??
Presuming we're just talking menswear...
Chicago, I'd say check out Indepence on oak. They sale Oak St. boots there and other niche mens' clothing/accessories. Also, Haberdash. You can check their site to get a feel for what they offer. There is typically a little more in store. There are technically three stores. The newest one is on Roosevelt in a condo complex, nice spot. Then there are two almost right next to each other on State street off of Ohio. One is formal, with suits and such and the other is casual, footwear, accessories etc. There is also a downstairs in that location and a classic barbershop. There is a classic barbershop in the Roosevelt one as well, that store is much larger than the others. If you stop in for a clean shave or buy from the 'apothecary', ask for Jeron. Good guy!
Umm, Suit Supply Chicago is nice. That's not specific to Chicago, of course though. The space is very nice! Huge outdoor space/deck to chill on with a beer while being fitted.
Notre Shop in Andersonvillem is another nice spot to check out. Menswear and a little high-end streetwear as well.
Sir & Madame is another spot worth stopping by.
if I think of anything else, I'll add on. Ty should chime in. He would know more than I do, I'm sure.
Enjoy your stay bro!