Von Dutch Trucker Hats

$300 gas station hat. Bankrupt by 2009. Peak Paris Hilton era.

Von Dutch Trucker Hats surged as a $300 luxury icon in 2003, fueled by Paris Hilton and Ashton Kutcher, but their mesh-backed design now signals a dated peak. The brand's 2009 bankruptcy followed a collapse from gas-station origins to overhyped status.

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