Boston & New England Relaxed Trucker Hats

Snapback Trucker

BOS Hockey Circle Emblem Performance Hat - Chowdaheadz

Performance Hats

Fenway Printed Patch Relaxed Trucker Hat - Chowdaheadz

Relaxed Trucker

Wicked Mass License Plate Washed Dad Hat - Chowdaheadz

Dad Hat

BOS Jump Shot Chunky Knit Winter Hat - Chowdaheadz

Winter Knits

Skip to results list

Boston & New England Relaxed Trucker Hats

Same great trucker, softer feel. Our relaxed trucker hats feature unstructured front panels that contour naturally to your head — broken-in feel from the first wear, breathable mesh back, adjustable snap closure, and a lower profile that works just as well on the boat as it does around town. With 110+ Boston and New England designs — Fenway, Boston skylines, shamrocks, Maine, New Hampshire, Vermont, Bigfoot Crossing, and more — there's a relaxed trucker for every kind of New Englander. Browse our full hats collection or check out snapback truckers and dad hats for more styles.