Why I Stopped: Wyll gives off that type of effortless cool that reminds me of a young Marlon Brando. He's sweet, suave, and knows how to own his style. None of this comes as a surprise once I tell you that he's a professional stylist for a pretty amazing agency here in Chicago. When I stopped him on the street, he was in the middle of running some errands. But let's be honest: running errands never looked so cool.
Let's start with that motorcycle jacket. I'm seeing them everywhere this fall, but Wyll knows how to make his stand out with a set of decorative pins that had me so excited (Anna Wintour! Johnny Cash! Cheap Sex!).
Maybe you've heard that adults shouldn't wear graphic tees. I call bullsh!t on that.* The key is knowing how to balance a heavy graphic with supporting neutrals. In this case, Wyll has tamed the loud graphics of his tee by framing them with black. What's more, the materials (jean pants and leather jacket) support the punk feel of the tee without distracting from the graphic itself. Whether it's obvious at first or not, Wyll has given grown-ass men everywhere a masterclass in pulling off the graphic tee.
Style Tip Challenge: Go bold! Be loud! Make a statement! Just don't leave a heavy graphic (or even a busy pattern) untamed or unframed.