Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest style seen in Chicago.

There are so many ways to make menswear fun. Sam did it by sporting bold prints on his blanket jacket, coordinating them with his playful scarf and cool porkpie hat. Also love his shoes (glossy but still casual) and folded hem. Smart choices for a musician—his look has depth, character and, above all, is pretty amusing. It’s always good to have something to look at while you listen.