While baseball caps date back to the mid-1920s, trucker hats only entered the fold in the late 1960s. They were, ... Matty Matheson’s workwear brand, Rosa Rugosa, makes its own trucker hat. The cap ...

Compared to baseball caps, the profile of trucker hats should be less rounded and more squared. Goorin Bros.'s, for instance, has that classic trucker look that is rugged and edgy. Advertisement ...

This cult classic cap from the ’90s is back. The Von Dutch trucker hat — most notably sported by multi-hyphenate style icon Paris Hilton, pop star Britney Spears and actress Lindsay Lohan ...

Akubras, berets, vintage trucker hats, pageboy caps, a good straw gardening hat—you may find yourself with one (or all) of the above in your wardrobe rotation at one point or another. Advertisement ...