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Bow-dacious Denim Jacket ($400) and Strong Seamed Denim Pant ($295)

"I wanted the bow lapel to look like it could come completely undone," Gurung says. "She goes out in this very chic, pretty package and at the end of the evening, her shirt's unbuttoned and the lapel unravels . . . it tells a little story." He suggests wearing it with the matching pant or a pair of really lived-in trousers for that "uptown/downtown balance — that's what makes the clothes interesting."