Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest style seen in Chicago.
Sheyssa's outfit is like a poem: the umbrella rhymes with the shoes, and the hat with the trench coat. Love the way she cinched it with a leather belt. And how she balanced the masculine hat with a fierce pair of leopard booties.
Sheyssa Rosado is also known as the Vintage Messenger—she delivers clothes right to your door. Find her here and on Instagram @vintage_messengers.
See more Chicago street style in the Chicago Looks blog.