Street View is a series in which Isa Giallorenzo spotlights fascinatingly fashionable Chicagoans.

Love how Britney made such a busy combination look so cool and understated. The fact that the only accessory she’s wearing is a hat balances it all. A fun detail: one of her shoes has laces, the other one doesn’t. It’s all planned, but somehow the result seems very relaxed.