Trucker Hats Are Making A Comeback — Yes, Really

Picture this: It’s 2003, The Simple Life just aired its debut season, and Paris Hilton and Nicole Richie are wearing trucker hats. Your crush, Ashton Kutcher, was just spotted courtside at the Lakers game wearing one, too. Now you want one, specifically from Von Dutch. A short while after, The New York Times deems them “not cool.” Defeated, you put the cap in a box in the back of your closet, where it has likely stayed for the past 15-plus years.

Cut to 2021. Visible thongs, platform flip flops, candy rings, and low-rise jeans are all gearing for a comeback. Y2K trends are, to the dissent of many who grew up in the aughts, all the rage. So naturally, the headgear beloved by ‘00s A-listers is also making its way back into fashion’s good graces. 

In April, Bella Hadid was spotted wearing low rise, baggy jeans with retro sneakers and a trucker hat while on vacation in Miami. Later in the month, Gigi Hadid followed suit, pairing her trucker hat — a custom style that says, “Gigi’s 26th on Bond St. Best Grilled Cheese In Manhattan,” on the front in honour of the model’s recent birthday party, which involved a grilled cheese food truck — with a sweatsuit and tall UGG boots. Rihanna, too, debuted a trucker hat recently, styling her Esso hat with an Adidas tracksuit, heeled Fenty flip flops, and a bowler bag from Prada’s collaboration with Adidas, while Gwen Stefani wore one to announce her engagement. 

If right about now you wish that you didn’t part with your Von Dutch trucker hat, you can still participate in the trend: The brand just reissued many of their early aughts styles, making the second coming of the hat style inevitable. According to Ed Goldman, the general manager of Von Dutch, when the brand started to notice a resurgence of other ‘00s-era trends, they saw an opportunity for a comeback. “Our brand is taking advantage of the shift by expanding our offerings with new, elevated styles, [while] staying true to the staples that made us so popular,” Goldman tells Refinery29. In its fall ‘21 collection, the brand included other ‘00s fashion mainstays like bowler bags, low-rise flare jeans, and crop tops with decals. Goldman says the uptick in popularity this year has been so significant that it’s easily comparable to the success the brand saw in the ‘00s. “The only difference is which celebrities and consumers we see wearing [our brand],” he says. 

And just like in their original heyday, trucker hats aren’t only for the rich and famous. They’re a huge hit on TikTok, too. On the Gen Z platform, #TruckerHats has 1.4 million views and is loaded with videos of users ranking their favourite “ugly” fashion trends, including trucker hats, and showing off their next-gen Von Dutch styles.  

Maybe it's just the cyclical nature of trends, combined with Gen Z’s obsession with styles from their birth years, that’s allowed for a Y2K fashion renaissance. That, or it’s rooted in the fact that so many people spent this year in their childhood homes, surrounded by their teenage belongings. Either way, trucker hats are back — and "that's hot."