We all feared this day would come, but I worry it is barreling toward us with worn down brakes. Or more fittingly, we are inching closer to the day when it’s going 55 in a 65 zone and seeing it in on a clogged freeway leaves you angry and cursing your bad luck as it sits there until you are spared and there’s an opening to pass it. But the road might be frustrating and arduous, we may be stuck once again with the trucker hat trend. It is simply the nature of the beast, fashion is a fickle machine, making strides to stay ahead of trends and doing whatever you can to stand out from the crowd. It’s why, after several years of pulled together men with nice fitting suits and trad sensibilities, we are embracing the comfort and disheveled look of birkenstocks, and “Dad jeans.” After years of suffering the uncomfortable effects (I don’t think I need to expand on this…) of drainpipe pant legs, this is a natural roundabout and while we may momentarily enjoy this period of put-together vintage ball caps, panama, and bucket hats, like sitting behind a slow-moving truck we are powerless to do anything but bide our time until this trucker hat trend too passes.
The trucker hat is a natural evolution from the baseball cap, featuring a breathable mesh and sweat-absorbing foam front that keeps trucker’s heads cool on long days spent on endless paths. They became an essential piece of the rural truckers uniform because companies like John Deere used them to promote their companies by giving them away to these workers. The hats were cheap enough to mass-produce and instantly made the wearer a walking billboard for the company. It wasn’t until young urban kids started wearing them in the early 2000s and they spread to the ranks of celebrity, gaining fans in Pharell, Ashton Kutcher, and Justin Timberlake that trucker hats for a brief time became “cool.” Nothing embraces the spirit of American workmanship like donning a trucker hat and it really only takes a single viewing of a Levi’s ad to confirm that this trend was a real and very powerful force.
While trucker hats will forever be a part of a uniform for those workers of the freeway, I fully expect these to be making a comeback on the runway. As we move toward comfort we might as well embrace this trend, instead of us feeling pressure to be fully dressed in the heat, maybe the relief of a trucker hat and birkenstocks will be a welcome respite. Or maybe we’re all just going to look like Ashton Kutcher grade d-bags.
If you want to fully take the plunge into this trend, check out this Y-3 hat on SSENSE. (It’s $65!!! This absurd price point is how you know we’re getting ourselves into some high-fashion trucker hat trouble.)

Justin Timberlake’s startling before-and-after shots are the perfect example of how fashion has evolved in the past 10 years.


