Von Dutch Trucker Hats

In 2003, Paris Hilton, Ashton Kutcher, and every person who watched The Simple Life made mesh-backed trucker hats a $300 luxury item. Von Dutch hats originally cost gas station prices, then celebrity endorsement inflated them into a status symbol. The brand filed for bankruptcy by 2009. The hat that was supposed to signal effortless cool now signals "I peaked in 2004." Ed Hardy filled the same niche a year later with bedazzled tiger graphics, and somehow aged even worse.