Similarly to trucker hats, the caps combine comfort ... A collaboration blossomed between Hood Hat and the preppy streetwear label, resulting in new hoods and colors to represent.

As if a preppy popped shirt wasn’t bad enough ... While hats have never gone out of style, puffy trucker hats were a staple at the turn of the century. Puffy, big, and loud — we’d happily ...

Funky trucker hats are all the rage with Gen Alpha, and apparently, they’re now preppy. These hats from Little Chicken Kids can be customized with the patch of your kid’s choosing, like a ...

And it definitely seemed to be targeting a preppy demographic. There's no sign of a black turtleneck here. Apple's vintage trucker hats make Ashton Kutcher the perfect choice to play Jobs in the ...