Lloyd Bishop/NBC
Grace Gavilanes
Sep 19, 2014 @ 7:13 am

Today, we raise a glass to one of the funniest men on late night TV: Jimmy Fallon. The newly minted Tonight Show host celebrates a major milestone, ringing in his 40th birthday in the midst of a super-successful career that boasts an Emmy win for his work on Saturday Night Live and a Grammy nod for his comedy album. The SNL alum even starred as InStyle’s Man of Style back in 2004 when he was merely 30—how's that for a flashback? "I've had many fashion disasters," he admitted to us. "I'm glad I had my sister ... someone who'll tell you when you're lame. Like when you're getting ready to go to school, and you're like, 'This bandanna is cool, man!'" Sound advice!

Travel back in time to see Jimmy Fallon's October 2004 Man of Style spread, plus more of Hollywood's most stylish men.

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