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

Fashion can be a balancing act. David’s outfit has a lot of details, but they all work together: the artsy loafers, the perfect hem length, the print of his socks, the vest, the tie clip, the lapel pin, the snug fit of his garments, the color coordination . . . I mean, he even matches his bike! The best—and hardest—part is that it all looks effortless, like he’s been doing this forever. And it’s true: David was once voted best-dressed in preschool. I guess it’s all a matter of practice to master the death-defying feat of dressing well.

See more Chicago street style in the Chicago Looks blog.