Hollywood’s Biggest Canadian Tuxedo Fails

So many jeans, so little time.

The Canadian Tuxedo is back in style this season, with everyone from Kendall Jenner to Kate Hudson rocking the jean-on-jean look. However, it’s a risky outfit, and poor execution can create fashion scars that will live forever. (See: Justin Timberlake and Britney Spears at the 2001 American Music Awards.) These 10 cringeworthy cases are so bad, they’re good just bad.

  • 1 Jay Leno
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    That chest hair, though. [/item
  • 2 Gwen Stefani
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    Stefani would have benefited from a more tailored suit. This Canadian Tuxedo is drowning her. [/item
  • 3 Michael Jordan
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    *Screams for fashion victory.* [/item
  • 4 Martha Stewart
    The queen of crafting wearing the queen of tragic outfits. [/item
  • 5 Riff Raff (and Katy Perry)
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    For some reason, this duo decided to pay tribute to Spears and Timberlake’s tacky matching outfit from 2001…and they managed to make it even tackier. Riff Raff’s studded jacket and Abercrombie-style pants are very unsettling. And Perry’s patchwork dress belongs in a campy rodeo, not the red carpet. [/item
  • 6 Kanye West
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  • 7 Sean Penn
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    Penn’s very proud of this outfit. (And he really shouldn’t be.) [/item
  • 8 Pete Wentz
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    While the bow tie is a classy touch, it doesn’t save this tear-inducing ensemble. Why would you subject the youths to this, Pete? [/item
  • 9 Jay Leno (Again!)
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    Repeat offender. But he did shake things up with a red T-shirt. Spicy. [/item
  • 10 Justin Timberlake (and Britney Spears)
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    The founders of the Canadian Tuxedo, tbh. [/item