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Before he was snarking it up on The Vampire Diaries, Ian Somerhalder was just another pretty face trying to make it as a teen model in the 1990s. In fact, Ian was the face of Versace back in 1995 — with his striking baby blues, shaggy hair, blond highlights, and signature pout, we’re not surprised by how many fashion powerhouses took notice of his striking good looks.

Ian got his big break in 2000 when he booked his first leading role on the small screen as Hamilton Fleming on the WB’s Young Americans. Unfortunately, the Dawson’s Creek spin-off was canceled after nine episodes, but Ian didn’t stop acting. He then went on to star in FOX’s breakout hit, Lost, before landing the role that would change his life forever in 2009 — Damon Salvatore on the CW’s The Vampire Diaries.

Ian has come a long way since his modeling days, and although he traded in his aloof stare for a sexy, albeit cocky, grin, he never lost his ability to make us swoon.

Check out Ian then, as a teenage model, and now, at The Vampire Diaries 100th episode celebration, and tell us what you think in the comments!

Crystal Bell is an editor at Wetpaint Entertainment and our resident fangirl for all things The Vampire Diaries. Follow her on Twitter and Google+!