When you think of Audrey Hepburn, Marilyn Monroe, James Dean, what comes to mind? Icons. Film. Fashion. All of these actors hit their movie sets and made a kick-ass outfit famous. With the best wardrobe stylist backing up our talents it still takes something spectacular to make an outfit an icon. With Sex and the City 2, a film that is more about what they’re wearing than what’s going on in the film, hitting theaters on Thursday, May 27, 2010, we thought we’d put a list together of the Top 10 Most Fashionable Characters of All Time!

Take a look…

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I don’t pay attention to major fashion magazines. I’m more into film trades or a good novel from time to time. Yet, every once in a while there’s that “special edition” or “collector’s issue” that comes out and gets me every time. This year my guilty pleasure is the latest issue of Vanity Fair. The above photo is just one of the many satirical images that feature some of today’s most popular funny men and women. The magazine highlights who they consider to be the new comedy legends of this generation. Some of their picks include actors who’ve just made their mark in recent years, while others have been around for ages.

More on Vanity Fair and the comedy legends photo spread after the jump.

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