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Hiker wearing artist series trucker cap by Sunday Aftternoons

Artist Series Truckers

Our own spin on the new "classic" trucker! Each hand-drawn design showcases the beauty of the great outdoors and provides groovy inspiration for all of your adventures. Ventilation? Sure. Wicking? Absolutely. But don’t try to go incognito—our Artist Series Truckers are wearable art sure to turn heads.

Trucker Hats now with StretchBack Sizing™!

Our patent pending StrechBack Sizing™ system combines classic snapback sizing adjustment with a little extra give that provides the perfect head-hugging experience. Try it on, we think you'll love it.

image showing the snapback sizing and dynamic stretch of Sunday Afternoons trucker hats

Carlos del Rio

Hailing from Mexico City, Carlos del Rio was formally trained in graphic design and illustration. Combining techniques of pointillism, ink, and watercolor, Carlos brings an unconventional approach to art and life.

Carlos del Rio Headshot

Chris Herbst

With flow as his guiding principle, Chris Herbst shares his love of the outdoors through his designs, teaching art, and creating surf and stand-up paddle boards in Southern Oregon.

Chris Herbst Headshot

Acacia Lacy

Combining her childhood memories and love of nature with ideas from the kids in her neighborhood, Acacia Lacy’s designs evoke the boundless imagination and wonder of youth.

Acacia Lacy Headshot

Jessilyn Brinkerhoff

Jessilyn Brinkerhoff brings an attuned awareness of her Southern Oregon home to her art. Her designs communicate and connect, giving voice to important ideas in her community.

Jessilyn Brinkerhoff Headshot


New Arrivals

New Spring/Summer 2020 Hats

Built for exploring the trail or a playful day at the beach, our new hats are loaded with adventure enhancing technology like...

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Recycled Collection

Recycled Styles

Six styles in our collection are now made from 100% recycled polyester main body fabrics. Our recycled polyester is high-performing and sourced from post-consumer recycled material made from plastic bottles...

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Heritage Collection

Heritage Collection

The Heritage Collection is constructed of super lightweight, waxed canvas. Finally a hat that can take you from the trail to a dinner reservation! Check it out.

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