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With a comfortably beat-up leather couch, a stained and yellowed British flag, and exposed brick walls painted black, Nolita's Barker Black outpost captures the spirit of a renegade Englishman with "subversive sophistication," much in tune with the brand's designers and shop owners, Derrick and Kirk Miller. Derrick, a former designer for Ralph Lauren, and his brother teamed up with the venerated, century-old brand to launch Barker Black in 2003, and they have kept the British handcrafted production standards intact while overhauling Barker's stodgy design in favor of a more punk aesthetic. The result: lighter, more wearable wingtips for distinguished gents, with quirky design touches like the Millers' trademark skull and bones logo. — Meredith Bryan