Who: The Vampire Diaries’ Damon Salvatore (Ian Somerhalder)
Why: Some looks may be timeless, but this centuries-old vampire knows the importance of updating his wardrobe with some trendsetting bite.
Style Tip: Whether mortal or immortal, nothing says “I’m trouble—and now I want to suck on your neck” better than a black leather jacket, T-shirt, and jeans.