Space 519 in 900 North Michigan bldg is extremely well curated and carries a lot more than just clothes. The guys used to run a place called Jake that is now defunct. It's a good place to gather inspiration from and one of the better informed places in Chicago.
Barney's Flagship at the corner of Oak and Rush has a good denim selection, among many other things. Chris is an informed, honest, helpful sales associate there.
Penelope's on Division in Wicker Park is quite good. Someone said they have never found anything interesting there. I find that hard to believe as I probably buy stuff from there 10x per year. Well curated despite the size and quite ahead of the curve for Chicago.
Haberdash on State is better than the one on Wells. But sometimes the sales associates try too hard. Not really "streetwear" but a cool shop.
Saks Men's on Michigan Ave is quite impressive. Make sure you take the elevator up to the 2nd and 3rd floors. SAs can be uppity, but a couple have great style.
Apartment Number 9 is a cool store (and a great song). A nice blend of sportswear as well as things that could be incorporated into a formal wardrobe.
As far as more name-brand brick and mortars, there is a Carhartt store now on Milwaukee in Wicker Park and the Levi's store on Mich Ave is usually pretty solid.
+1 on Publican, Avec, Xoco. I would strongly advise against any Rosebud affiliated restaurants. If I were gonna do a chain affiliated restaurant, I'd stick with Lettuce Entertain You spots. For other food spots relatively near touristy areas, I'd recommend Naha, Purple Pig, Sepia, Al's Italian Beef, Gilt Bar, Twin Anchors.
