Trucker hats were this trend that we all seemed to get sucked into, even though none of us really understood why. It was as though we saw Ashton Kutcher wear it one time and then we were all hooked. All the celebrities from the early 2000s were guilty of wearing a trucker hat, and most of them were made by Von Dutch. Former *Nsync member Justin Timberlake wore oneArchiesJournal8 Simple Rules star Kaley Cuoco wore oneWetPaintPop Princess Britney Spears wore oneRex/ShutterstockAshton Kutcher wore them all the timeE OnlineLindsay Lohan had them tooStephen Lovekin/Film MagicParis Hilton and Nicole Richie