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Italian label Replay is all about aggressive mixing and matching. Plaid is paired with floral designs, grungy, masculine pieces are combined with feminine beading, and even the store itself—a large, immaculately clean space—is littered with tattered garage-like artifacts. And in keeping with the dinge-chic esthetic, Replay focuses strictly on not-for-the-office attire. Even the higher-end We Are Replay line—which boasts handmade items often emblazoned with the word “replay”—primarily consists of jeans, patched sweaters, shirts, and boots, most of which soar well into the three figures. The results are predictably eclectic, with some items that look like an arts and crafts teacher took a glue gun to them, and others that appear one step ahead of tomorrow’s fashionista. — Melissa Noble

Prices drop as much as 50 percent during end of season sales in winter and summer.