Trucker Hats: The Fashion Statement That Refuses to Die

June 03, 2016 by Tiffany Hsu, @tiffkhsu

There are few accessories the style police love to hate more than trucker hats.

The mesh-and-foam headwear once popularized by stars such as Justin Timberlake and Ashton Kutcher has lurked for years on the fringes of fashion. But now, it’s staging a return.

Ashton Kutcher Headshot Teenage Millionaire Trucker hat

Ashton Kutcher (Photo: Flickr)

Kendall Jenner – model-of-the-moment and Kim Kardashian’s younger sister – may be most responsible for the comeback. When not stalking runways for Chanel and Oscar de la Renta, Jenner has spent the past year being photographed in various trucker hats.

In April, she posted a paean to the look on her personal blog: “For me, the trucker hat = SPF + paparazzi control! So, why exactly did they ever go out of style in the first place?”

This spring, Jenner’s even-younger sister Kylie publicly donned the $39 Von Dutch OG Patch Denim trucker hat, possibly as a paid endorsement. The style sold out within a month, along with 25 percent of the other trucker hat options Von Dutch boasts on its website.

That’s the same Von Dutch brand most associated with last decade’s trucker hat craze.  Paris Hilton, Lindsay Lohan and seemingly every other icon of the aughts worshipped at the Von Dutch altar.

“These celebrities have such influence on fashion culture that whatever they do, it’s likely to be copied – it’s so coveted and crazy,” said Scarlett Newman, a master’s degree student in fashion studies at the City University of New York who specializes in the intersection of fashion and pop culture. “If it’s on a Kardashian, the trucker hat will have some sort of resurgence, no doubt.”

But like so many other cultural phenomena before it, the trucker hat has humble roots.

Though similar to the classic baseball cap – currently known as the “dad hat” – the trucker hat is distinguished by a sweat-absorbing foam front, a breathable mesh backing and an adjustable closure. In the 1980s, companies such as agricultural equipment giant John Deere mass-produced the hats, emblazoned them with corporate logos and handed them out for free in rural communities.

The so-called gimme hats were a model of blue-collar comfort and practicality. Truckers wore the one-size-fits-all headwear to keep sun and perspiration out of their eyes during long drives.

The hats “have long been a symbol of working-class anti-fashion,” according to author Jennifer Grayer Moore in her 2015 book “Fashion Fads through American History: Fitting Clothes into Context.”

“Thus the promotion of the caps as trendy and chic was paradoxical, incongruous, and potentially mocking of the origins of the hats,” Moore wrote.

A photo posted by King Kylie (@kyliejenner) on

By the early 2000s, the chapeaux had morphed into an ironic hipster take on mall-chic, a frat guy delight. Rapper Pharrell Williams was rarely seen without one. He’s since moved on to a so-called buffalo hat that makes him look like a Canadian Mountie officer.

In 2004, the band Bowling for Soup paid tribute to the trend in their album “A Hangover You Don’t Deserve.” The three-minute song “Trucker Hat” – which also discusses the regrettable parachute pant fad – compares a lover to the hat.

“It’s easy to see/I’ll never go out of style on you/And nothing really feels the way you do/Nothing in the world could ever make me look as good/When you fit me like you do.”

Newman, the CUNY student, was then in middle school.

“There was a moment when I saw Britney Spears in one, and I asked for one too,” she said. “My mom was like, ‘What? No.’”

But fashion is “incredibly cyclical,” Newman said. “If the hat comes back, it will definitely have a new meaning for the generation after me – for younger kids, it’s something different to explore.”

Tilly’s has more than 200 different trucker hat styles on its website. Men can purchase the Volcom “Liberal Cheese” style for a mere $19.99. Women can grab the Billabong “Pit Stop” look for even less.

Current trucker hat fans include Jenner pal Gigi Hadid – another young model who’s made something of a second career exhuming overalls and other ancient fashion relics.

Enfant terrible Justin Bieber, known nearly as well for his extravagant collection of outrageous headwear as he is for his music, has made several recent appearances with trucker hats perched precariously on his well-gelled coif.

He wore one while vacationing with model Hailey Baldwin. Another debuted on the “Tonight Show with Jimmy Fallon.”

In February, Bieber performed at the 2016 Grammys in a simple black trucker hat and a leopard-print jacket by Yves Saint Laurent.

Incidentally, that’s the same esteemed luxury fashion house that currently sells a trucker hat with a front panel featuring a calming scene of palm trees at sunset.

Price: $275.

Editor’s note: Because of an editing error, an earlier version of this report misspelled Kendall Jenner’s first name as Kendal.