Phalair Carter has to be one of the most well-dressed men in Chicago. I spotted him randomly on a quick lunch visit to Topshop with a coworker at the corner of Chicago and Wabash Avenues. Phalair’s use of contrasting patterns (stripes and checks) is what caught my eye. I wish more men were willing to experiment with color palettes and prints like Phalair, although let’s not kid ourselves. Dressing like this takes a man with a great, innate sense of style.

Tattoos plus classic men’s fashion made Gianpaolo and instant catch for my blog. Oh, hello there… (!)

Gianpaolo’s hair was perfect, his beard precisely trimmed, and the denim pants were creased and cuffed with vast attention to detail. Suspenders are becoming more popular in Chicago. I’m not a man so honestly I have no idea what drives men’s fashion trends, but I’m always happy to meet a guy who put serious thought into dressing well for the day.