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

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Sharon takes personal style to a whole other level with her early-Madonna-inspired ensemble. The worn-out booties ground her ethereal look and add a tomboyish touch to her supergirlie outfit. She made these opposite elements work seamlessly and finished them up with a savvy selection of accessories. I mean . . . how bold is that red flower? How adorable is that kitty purse?