16. Justin Timberlake

Justin Timberlake often comes off as the guy you want to hate, but really can't. Whether he was banging Mila Kunis on-screen in Friends With Benefits or going through the history of hip-hop (yet again) with Jimmy Fallon, he did it all with a coolness most guys aspire to. His vanilla style is consistently on-point without being too inaccessible (case in point: adidas Samoas), which enhances his natural charm. Looking good doesn't have to mean looking boring though, JT. How about in the new year you take a few more style risks?