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Kiefer Sutherland in a dress on Letterman: The shoes are all wrong

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Last night, 24‘s Kiefer Sutherland appeared on the Late Show with David Letterman and opted for an interesting wardrobe choice: a dress paired with a long-sleeved tee and combat boots. Sutherland admitted that he lost a football bet to a friend and this was his punishment. Or was it ours? Kiefer, if you’re gonna put on a dress, at least give us something pretty to look at! And pair it with some nice shoes! Next time you lose a bet, gimme a call and we’ll head on down to Christian Louboutin for a little shopping trip. It’ll be fun. That would be preferable to last night’s ensemble, which kinda looked like something Winona Ryder wore in Reality Bites. Not good.