10 of Fashion's Biggest Blunders


Trucker Hats

Nothing says "idiotic early millennium hipster" quite like the trucker hat. Cocked to the side, preferably emblazoned with an ironic saying, maybe paired with a pair of thick, black-framed glasses, it's the calling card of posers everywhere.

Trucker hats might have had their moment back in 2000 or so, when they were confined to an incredibly hip neighborhood in Brooklyn or somewhere -- but when you can buy an item at a mall kiosk, guess what? It's not hip anymore. And Paris Hilton has worn them, for goodness' sake. They clearly jumped the shark years ago, so let's put trucker hats to rest -- until the next generation of hipsters unearths them in 2036.