Von Dutch Trucker Hats

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, with celebrity endorsement inflating prices by over 500%. Outperforming #5 Ed Hardy's bedazzled decline, these hats aged worse than the typical fad due to their fleeting cool, fading into irrelevance within six years.