Usher loves looking dapper, and what better decade to draw inspiration from than the 1920s? The singer sports a double-breasted waistcoat and two-toned shoes along with some modern bling at the Grammys (left) while his 26th-birthday party suit (right) is a "very early Fred Astaire look," says Kaufman. "The top hat, the white gloves, the cane, the longer jacket – it's that kind of free-swinging, '20s party mode."