Kylie Jenner's IG and Shutterstock

Remember the Von Dutch trucker hats Paris Hilton and Britney Spears popularized in the early ’00s? It’s almost as unforgettable as the celebrities and their inane antics. For those who are unfamiliar with the trucker hat (or are too young to remember), the trucker hat was a popular and somewhat controversial fashion staple of the ’00s.

As early as 2001, the hat was spotted on the ever-fashionable Pharrell Williams. The trend quickly caught on so that by 2003, Johnny Knoxville of Jackass was seen sporting the boxy cap. But it was Ashton Kutcher (on MTV’s Punk’d) where the trucker hat became weirdly iconic. Rarely was Kutcher seen without the hat, making him the poster boy for Von Dutch.

Founded in 1947 in Compton, California, the Von Dutch namesake stems from the nickname of Kenneth Howard, otherwise known as “Von Dutch.” Howard was a prominent designer in South LA who is considered the father of modern pinstriping. It was not until later under the direction of his daughters that the under-the-radar company began producing the now-infamous trucker hat.

Today, the name Von Dutch tends to evoke the memory of the notorious trucker hat more than its company’s founder. And since Kylie Jenner posted a selfie on Instagram wearing one of the hats, rumors of an unexpected return of this piece have surfaced.

That said, it may be time to reflect more on the history and styling of the hat. So whether you are inspired by Justin Timberlake sporting the hat at the Grammy’s, or the more casual approach of Britney Spears pre and post-rehab, be assured that the hat has range – both on and off the red carpet.

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Words by Molly Hannon
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