Stupid Canadian Beret

Canada has a military?

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Stupid Outdoor Hat

Stupid Outdoor Hat

Who the hell would ever wear this ugly thing?

Stupid Umbrella Hat


Worst hat ever?

Stupid Mexican Hat

Chihuahua's Stupid Hat

Stupid hat on a stupid dog.

Leighton Meester’s stupid hat

Leighton Meester's stupid hat

Sorry, Leighton Meester, you’ve got a stupid hat.

Woody Harrelson’s stupid hat

Woody Harrelson's Stupid HatWow, that is one dumb hat, and you look stupid in it, Woody Harrelson. I know you’re trying to pull off classy, but you’re just not getting it.

Stupid polo helmet

stupid polo helmet
Great wardrobe choices, dude. As if polo wasn’t aready ridiculous enough.