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2016 Winner: Bobby Garnett

Boston lost its most stylish son in May with the passing of Bobby Garnett, who scoured thrift stores and flea markets for treasures to fill his Strutters shops in Brookline, Provincetown, Allston and Back Bay before establishing his namesake vintage store, Bobby from Boston, in the South End in the 1990s. Ever since, its leather duffels, letterman jackets, newsboy caps and colorful bow ties have made it a destination for dapper gents, not to mention costume designers for period films from Ali to The Aviator. His eye was legendary, but he proved that a warm and welcoming smile is the best accessory of all.