Show (Air Dates): Glee (2009-present)
Actor: Chris Colfer

A fashion fan and proud of it, Glee pretty boy Kurt Hummel always surprises us with his inventive get-ups and, specifically, his stellar jacket collection, which includes everything from bright-red nylon getups worn over a shirt and tie, trenches with dramatic collars, and his envy-inducing navy blazer that's trimmed in red and finished off with gold buttons and a stamp of his school's crest. Cue the "So Fresh, So Clean" cover.