Sunday Afternoons Watershed Trucker

Ventilation? Sure. Wicking? Absolutely. But let’s be honest—our Artist Series Truckers are wearable art that simply looks great.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Ventilation? Sure. Wicking? Absolutely. But let’s be honest—our Artist Series Truckers are wearable art that simply looks great.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Designer and illustrator Jordan Ballard is inspired by the intricate shadows of the imagination. His unique style is reflected in the Dream Seeker Trucker, the newest member of our Artist Series Cooling Truckers. With Coolcore® wicking sweatband and underbrim, this trucker keeps you comfortable when outdoor adventures heat up. Braided cording detail adds an artistic touch while StretchBack Sizing™ ensures a customized fit.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Designer, illustrator, and photographer Dan Fredman of Portland, Oregon channels the power of the ocean with one-of-a-kind artwork featured in our Into the Blue Trucker. With classic trucker styling and modern technical features such as a bluesign® brim and wicking sweatband, StretchBack Sizing™, and mesh ventilation, with this hat, you also get wearable art. Features & Specs 2¾" Brim Length Classic trucker mesh ventilation One of a kind artwork Wicking sweatband StretchBack Sizing™ bluesign® brim and sweatband Patent pending Weight: 2.7 ounces/77…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

The creative artistry of the Artist Series Patch Truckers makes these six-panel, midheight ballcaps a stylish choice for your outdoor adventures. These nature-inspired designs, with one-of-a-kind artwork, feature a woven patch on the front panel. Made with PFAS-free DWR and 100% recycled bluesign® main body and mesh fabric. StretchBack Sizing™ and a wicking sweatband provide comfort and a good fit.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Artist Acacia Lacy lends her talent to the Kids' Artist Series Trucker. The wild bird theme features the hummingbird with proceeds going to benefit the Klamath Bird Observatory, working to protect wild birds in southern Oregon. Features the classic mesh ventilation you expect from a trucker, along with a bluesign® brim, wicking sweatband, and adjustable sizing.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Danielle Quigley's take on the majestic Rocky Mountains will take you there and back again in comfort and style. The Midnight Mountain Trucker is the latest in our limited edition Artist Series collection and features bluesign® brim and wicking sweatband, StretchBack Sizing™, and mesh ventilation. Designed for outdoor enthusiasts who appreciate a classic trucker that looks as good as it feels, you'll love this hat.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Designer, illustrator, and photographer Dan Fredman of Portland, Oregon captures the majesty of the mountains with one-of-a-kind artwork featured in the Mountain High Trucker. With classic trucker styling and modern technical features such as a bluesign® brim and wicking sweatband, StretchBack Sizing™, and mesh ventilation, this hat does the trick. Features & Specs 2¾" Brim Length Classic trucker mesh ventilation One of a kind artwork Wicking sweatband StretchBack Sizing™ bluesign® brim and sweatband Patent pending Weight: 2.7 ounces/77…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Featuring a magical design by artist Acacia Lacy, the Pond Party Trucker is sure to bring delight to kids and everyone they meet. With classic trucker styling and modern technical features, such as a bluesign® brim, wicking sweatband, and mesh ventilation, these hats make every day feel like an outdoor adventure. Features & Specs 2" brim Strategic crown ventilation Limited edition artwork Wicking sweatband Adjustable…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Rock a cap that's got personality for days. This curved bill trucker hat features hand-painted artwork from local designer AK Art Factory, giving you a one-of-a-kind vibe that stands out from the crowd. The breathable mesh keeps things cool while the adjustable snap closure fits just right. Perfect for anyone who wants to wear art on their head. Washable By AK Art…

by Bottoms Up Boutique · Anchorage, AK

🚚 Ships from Alaska

Artist Acacia Lacy lends her talents to our smallest version of the Artist Series Trucker, this time just for toddlers. The wild bird theme features the osprey and hummingbird with proceeds going to benefit the Klamath Bird Observatory, working to protect wild birds in southern Oregon. With the classic mesh ventilation you expect from a trucker, this mini version features a soft, crushable bluesign® brim and wicking sweatband.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Rock a cap that's got personality for days. This curved bill trucker hat features hand-painted artwork from local designer AK Art Factory, giving you a one-of-a-kind vibe that stands out from the crowd. The breathable mesh keeps things cool while the adjustable snap closure fits just right. Perfect for anyone who wants to wear art on their head. Washable By AK Art…

by Bottoms Up Boutique · Anchorage, AK

🚚 Ships from Alaska

Made from super cozy, breathable 100% recycled single-layer fleece, the Kids’ Cozy Critter is extra insulative for outdoor winter play. A super warm ear band keeps kids comfortable when the weather turns cold and the braided tassel on top and canvas animal patch make this hat extra fun. An interior loop makes hanging dry a breeze. UPF 50+ rated for sun protection. Features & Specs 100% recycled, breathable fleece Double-layer fleece earband Animal motif patch Decorative braided tassel Interior drying loop bluesign® main body fabric UPF 50+ sun rating Weight…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

With a classic profile that leans more urban than country, the Winston is a three-season hat that offers UPF 50+ sun protection for all your adventures. With a tall crown, flat, contemporary brim and metal eyelet and logo detail, the 100% wool felt makes this stylish hat breathable, insulative, and stain resistant.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

A trucker cap in a kid-friendly size! Limited edition artwork by Acacia Lacy inspires outdoor curiosity. Featuring a wicking sweatband and adjustable sizing for years of active play. Features & Specs 2 3/8" (6.3cm) pre-curved brim bluesign® brim fabric 100% recycled mesh ventilation One-of-a-kind artwork 100% recycled bluesign® wicking sweatband Adjustable sizing Weight: 2.2 ounces/62.4 grams Material Content: Brim: 100% Cotton, Front Crown: 100% Polyester, Crown Mesh: 100% Polyester, Exclusive Of Decoration Pack with care Hand Wash Cold, Do Not Bleach, Line Dry, Do Not Iron, Do Not…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

With a downsloping, wired brim that looks sharp up or down, the Natural Blend Kettle is two hats in one, with natural cotton/recycled polyester fabric on the solid side and 100% recycled polyester on the print side. UPF 50+ sun protective and PFAS-free durable water repellent.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

When skies are stormy and adventure calls, you need a hat that’s up for the job. The Ultra Storm Bucket is 100% waterproof, seam-sealed to keep you dry and comfortable while the downsloping brim helps rain roll right off. UPF 50+ sun protection makes it a great choice when the sun peeks through, and reflective piping helps when night falls. Packable and crushable, with a PFAS-free water repellent finish that repels moisture to avoid saturation.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

The classic design of the Nordic Snowflake Beanie takes us back, while technical details ensure your cold-weather gear is as innovative as possible. With two sizes to choose from, a perforated hole pattern makes it easier to hear. The fitted crown on this stylish skull cap is made from ultra-soft acrylic knit with a double insulated layer for comfort and keeps you warm when temps drop. It even looks great once the sun goes down and the fun moves indoors.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Made from ultrasoft acrylic knit, the Myriad Reflective Beanie is reversible with two colorful options: striped on one side and solid on the other. Integrated, reflective thread catches light when the sun goes down. As the days shorten, this beanie will help you go with the flow, no matter what the weather brings.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Looking for a stylish addition to your winter wardrobe? Look no further. Made from 100% wool felt, with a lovely leather hatband, the Taylor Hat takes things up a notch in any season. Easy to care for and packable, this snazzy stunner is going places. Features & Specs UPF 50+ Sun Rating 3" Brim 100% Wool Felt Naturally Water Repellent Genuine Leather Hatband Elasticized Wicking Sweatband Packs for Travel Weight: 4.6 ounces/130.4 grams California Residents see PROP 65 WARNING below. For more information, please visit our FAQ page here .

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Made from a recycled poly/paper blend and featuring a 100% recycled bluesign® wicking sweatband, the Sojourn Hat prioritizes style and sustainability, and is ready to step in as your new favorite sun hat. UPF 50+ sun protective with an extrawide brim for added coverage, this hat also features an adjustable chinstrap and hidden hook-and-loop sizing to help it fit just right. A decorative grosgrain hatband adds a classy touch to this sophisticated fedora.

Fashionable and bohemian, the Vivian Hat flaunts a floppy brim look for style and sun protection. Show off your avant-garde side with this fashionable wide brim floppy look. Warm, cozy, and made of 100% wool felt, the Vivian offers UPF 50+ sun protection while maintaining breathability, and moderate to cold weather comfort.

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

Made from ultra-soft acrylic knit and double-layer insulated for comfort, the Nightfall Reflective Beanie is sure to become your favorite go-to skull cap. Stitched with reflective fiber woven into the yarn, this beanie sports a fun heathered pattern by day and reflects with a little flash and flair in low light. Reversible with a fitted crown for a snug fit, you won’t want to take this beanie off!

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon

A trucker cap in a kid-friendly size! Limited edition artwork by Acacia Lacy inspires outdoor curiosity. Kid-proof features and adjustable sizing for years of active play. Features and Specs 2 3/8" (6.3cm) pre-curved brim bluesign® brim fabric 100% recycled mesh ventilation One-of-a-kind artwork 100% recycled bluesign® wicking sweatband Adjustable sizing Weight: 2.2 ounces/62.4 grams Material Content: Brim: 100% Cotton, Front Crown: 100% Polyester, Crown Mesh: 100% Polyester, Exclusive Of Decoration Pack with care Hand Wash Cold, Do Not Bleach, Line Dry, Do Not Iron, Do Not Dry…

by Sunday Afternoons · Ashland, Oregon

🚚 Free shipping on orders over $39 · Ships from Oregon