Inspired by the Fantasy Fasion Legaues that have been cropping up online, we drafted an All-Star team of the strongest spring looks for our Chicago guy. Heres how we would play it this season:

The Avant-Gardist
The Corporate Shark
Giorgio Armani will help him match the other creative nonconformists at HotHouse. (No one has to know it’s not vintage.)
For an aspiring Ari Gold, a slick suit from Burberry will work. We predict that he will strike a deal on that sweet West Loop loft.
Giorgio Armani, 800 North Michigan Avenue.
Burberry, 633 North Michigan Avenue.
The Urban Prep
The Man in Black
In Ermenegildo Zegna for the weekend, he will be just as comfortable shopping in Wicker Park or having brunch with her parents in the burbs.
For the off-duty rock-star look, we like Michael Kors. Perfect for making an appearance with the guys at The Underground, the much-talked about new nightspot.

Ermenegildo Zegna, 645 North Michigan Avenue.

Bloomingdale’s, 900 North Michigan Avenue.