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


You wouldn’t know by looking at his weekend-warrior threads, but Diego Acosta makes his living as an accountant in the sartorially staid world of corporate finance. “Most guys at the office wear basic plaid collared shirts with slacks, but I like to do something different,” he says. “For example, I will sometimes wear a white waistcoat with neutral color block [paired] with sleek silk black slacks. I try to limit one striking garment or color combination per outfit.” His ideal nine-to-five ensemble? “One that emphasizes my body, particularly my legs. So three-inch inseam shorts with a graphic tank top and gladiator sandals, paired with a snapback hat and/or a man bun.” Acosta’s gutsy fashion choices started in his youth, as a way to rebel against restrictive social norms and a conservative household. “That boldness, I believe, is what people connect with on a deeper level rather than the actual look itself,” he says.

See more street style in the Chicago Looks blog.