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

Menswear is all about the right fit and throwing in a few smart accessories—which Andy seems to be well aware of. His jacket hugs his shoulders perfectly and his skinny jeans were made for his slim build. Top that with a cool winter hat, a respectable leather briefcase, shiny combat boots, and a power watch and he’s good to go. His shirt buttoned up all the way to the top gives the look a welcome nerdy/hip touch.