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

Layers, layers, layers—Rachel knows the secret to sucky-weather dressing. I’m digging her roomy shearling jacket on top of a dark 80s floral-print blazer, which is on top of a dainty knit cropped top, which is on top of a T-shirt. From roomy to dainty, she covers it. Plus, the girl can (subtly) accessorize; just check out that beanie, the pendant, the boyish vintage digital watch, the houndstooth socks . . . All in tune with her street-smart vibe.

See more Chicago street style in the Chicago Looks blog.