Home ยป Oscars 2009 Best and Worst Dressed Men

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Best

Will Smith

Will Smith’s shawl-collar, double-breasted tuxedo stands out in a good way. It fits him perfectly. He tied his own bow-tie and remembered to wear shirt studs. The shawl lapels are wide enough that he can even pull off a broach.

Dev Patel

Dev Patel is a skinny dude so he wore a skinny tux. It’s slim-cut single-button with a narrow shawl lapel. His bow-tie is the perfect size and the shirt’s ruffled placket is a neat touch, too bad the sleeves weren’t a bit longer. The flap pockets are also unfortunate.

Hugh Jackman

Hugh Jackman’s main costume was a perfect classical tuxedo with a shawl-collared vest. The only problem with his outfit was the shirt buttons, which is a mistake also made by a lot of his guests.

Mickey Rourke

We expect Mickey Rourke to be dressed crazy, but his white suit with black vest was actually kind of a reasonable way to say “fuck convention”.

Honourable Mention

John Legend

John Legend’s brown suit-tuxedo is bad (worst dig: “was he sponsored by UPS?”), but if you must wear a four-in-hand tie, as many stars do, you should at least kick it up a notch with a tie clip or pin.

Worst

Brad Pitt

Given that he’s one of the most-photographed people there, you think he’d get a real bow-tie. Maybe he could have asked his dozens of nannies if any of them know how to tie one? Brad Pitt’s tuxedo was lacking in all sorts of other details.

Philippe Petit

I’d like to think that Philippe Petit’s weird shiny suit and dandified white scarf were some kind of commentary on America. But I suspect the real explanation is that French entertainers dress just as badly as entertainers in other countries.

Philip Seymour Hoffman

Philip Seymour Hoffman looks like he’s attending his own funeral, but that’s better than last year when he was attending his own prom. I’m not even going to mention the toque.

Sean Penn

Sean Penn wore the worst of all possible shirts. First, it’s nearly as dark as his tux (midnight blue rather than black), which is a cool look if you’re an appropriate age to date Miley Cyrus. Second, the collar doesn’t fit, so he has to leave it unbuttoned. And finally, it’s a button-down collar, which I don’t like for casual wear but can’t even conceive of for formal wear – and he makes it even worse by undoing the buttons! Amazing.

Written by Jared

February 23rd, 2009 at 6:17 pm

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2 Responses to 'Oscars 2009 Best and Worst Dressed Men'

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  1. Button-down collars are the work of Satan.

    Jack

    23 Feb 09 at 6:21 pm

  2. [...] Compare to the 2009 Oscars. [...]

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