Sunday Afternoons Mountain High Trucker

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

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

Bask in the beauty of the forest everywhere you go in our Woodland Trucker, one of the newest additions to our collection. With smart features such as a moisture-wicking sweatband and strategic crown ventilation, you get comfortable protection that won’t quit. Limited edition artwork by Mexico City’s Carlos del Rio turns this hat into wearable art that turns heads. Features & Specs UPF 50+ Sun Rating (mesh not rated) 2¾" Brim Length Strategic Crown Ventilation Limited Edition Artwork Wicking Sweatband Adjustable Sizing Weight: 2.7…

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

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

Meet the Scout Trucker Hat, a mid-crown, 5-panel trucker with a slight curve brim that offers timeless style and comfort. Its terry cloth sweatband and finished interior with custom seam tape ensure you stay cool and comfortable all day long. The adjustable back closure provides a perfect fit for any adventure.

by Pistil · Portland, Oregon

🚚 Ships from Oregon

Gear up for outdoor adventures with our Tip Top Hat, a mid-crown trucker featuring a distinctive mountain graphic on the foam front panel. The adjustable back closure ensures a personalized fit, while the terry inner sweatband adds comfort during active pursuits. Stay cool and stylish with the mesh back panel, making this hat the perfect companion for your next exploration.

by Pistil · Portland, Oregon

🚚 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

This foam trucker hat captures the wild spirit of Montana with a bold, eye-catching design. Featuring a structured foam front and breathable mesh back, it delivers all-day comfort with a lightweight feel. The graphic showcases a striking blend of mountain peaks, a powerful bear, and vibrant Big Sky hues, giving it a rugged yet modern edge. Finished with a curved brim and adjustable snapback, this hat is built for adventure—whether you’re exploring the outdoors or repping Montana wherever you go. A Montana Scene Original Design. All designs are property of The Montana Scene.

by The Montana Scene · Kalispell, MT

🚚 Ships from Montana

Hit the slopes in style with this mountain-inspired trucker hat. The front panel features a vibrant alpine scene complete with snowy peaks, pine trees, and a pair of skis ready for adventure. Designed with a classic brown bill and mesh back for breathability, this cap blends outdoor function with eye-catching design. Whether you’re après-ski or just dreaming of the mountains, it’s the perfect hat to bring a touch of winter wanderlust to your everyday look. A Montana Scene Original Design. Printed in Montana. All designs are property of The Montana Scene. All rights reserved.

by The Montana Scene · Kalispell, MT

🚚 Ships from Montana

This Ocean Pacific 5-panel trucker hat features a grey and blue color scheme, with a 2.75" brim and a 59cm size. The sublimated foam front logo and back mesh panels provide breathability and style, while the adjustable snap back closure ensures a perfect fit. Made with durable polyester material and featuring the iconic blue Ocean Pacific logo, this hat is a must-have for any outdoor adventure. Features : Color: Grey / Blue Material: Polyester Brim Size: 2.75" Blue Ocean Pacific Logo Size: 59cm Adjustable Snap…

by San Diego Hat Company · San Diego, California

🚚 Ships from California

This foam trucker hat blends classic Western attitude with everyday comfort. Featuring a structured foam front and breathable mesh back, it’s built to keep you cool whether you’re out on the ranch, at a rodeo, or just riding through town. The bold graphic front adds a rugged, standout look, while the curved brim and adjustable snapback ensure the perfect fit. Durable, lightweight, and made to handle long days under the sun—this is your go-to lid for wherever the ride takes you. A Montana Scene Original Design. All designs are property of The Montana Scene. All rights reserved.

by The Montana Scene · Kalispell, MT

🚚 Ships from Montana

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

Ladies, bask in compliments, not harsh UV rays! Wide brim and pleated neck cape protect with feminine grace. Design details like adjustable sizing, chinstrap, interior wicking sweatband and a ponytail-friendly opening prove the Sundancer has style AND substance. A favorite of gardeners everywhere, this hat is equally at home anywhere in the outdoors.

by Sunday Afternoons · Ashland, Oregon

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

“Lightweight and breathable, this sun hat features an interior sweatband for the hottest days. Plus, it's packable, and the brim can be worn up or down.” — Oprah Daily Carefree and casual, just like its namesake island! When the temps rise, you’ll reach for the Kauai for that cooling bit of shade and breathability. The upturned kettle brim puts a gleam in your eye, and the matching hatband adjusts to size. The Kauai compresses down to squeeze into even the most overpacked luggage, right next to your souvenirs.

by Sunday Afternoons · Ashland, Oregon

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

UPF 50+ sun rated with a textured weave and wide brim, this stylish hat adds a touch of flair to your wardrobe. No matter where your adventures lead, this hat adds just the right amount of shade. Internal adjustable sizing and breathable construction ensure a comfortable fit.

by Sunday Afternoons · Ashland, Oregon

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

Feeling foxy? The embroidered friend on our Kids’ Winterland Fox Beanie is almost as cute as the kids who wear it. Made from ultra-soft acrylic knit, the double-layer insulation keeps your kids extra warm. The reversible design means you get two hats in one. Hooray! Features & Specs Ultra soft acrylic knit Double-layer, insulated comfort Reversible to plush yarn interior Patterned exterior, solid interior Embroidered animal detail Fitted crown Weight: 2.29…

by Sunday Afternoons · Ashland, Oregon

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

The Vail takes style-conscious ladies to modern frontiers. Soft, warm wool felt in a Western-inspired silhouette feels at home even on urban ranges with a decorative hatband in multicolored beads. Internal adjustable sizing and sweatband make it feel as good as it looks. This hat makes a statement with both dresses and jeans, and looks smashing accessorized with boots and scarves.

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

Take your chill to a whole new level with the Unwind hat. This mid-size fedora is made from 100% natural Mexican tripilla straw and has a 3” brim for excellent UPF 50+ sun protection. The elasticized sweatband ensures a comfortable fit while the genuine leather hatband adds a classy touch. Dress it up for an evening out, or keep it casual for an afternoon by the pool, just relax and unwind.

by Sunday Afternoons · Ashland, Oregon

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

“Plus, there are three features we love: integrated sleeves that hold sunglasses in place, a hidden interior pocket and an adjuster to fine-tune your fit. This is the Swiss army knife of sun hats.” — HGTV The Sun Tripper Cap loves the meandering backcountry trail just as much as it loves after work happy hour with friends. The innovative Clamshell Brim™ folds down to almost nothing so you’ll have reliable sun protection no matter where your day takes you. Performance fabrics and a ventilated design ensure a comfortable fit and major style points. Smart and good-looking?

by Sunday Afternoons · Ashland, Oregon

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

The Kestrel Hat is our playful, relaxed take on the modern cowgirl hat. Made from a poly/paper blend with a 100% recycled bluesign® wicking sweatband, this hat’s shapeable brim offers multiple looks. With a leatherette-and-stone hatband for added flair, it also offers UPF 50+ sun protection.

by Sunday Afternoons · Ashland, Oregon

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

Little beachcombers need big sun protection, which is why we designed a Sun Guardian Hat just for kids. This lifeguard-style sun hat is made from 100% natural straw with a broad, downsloping brim with dark underbrim to reduce glare. The brim and top-of-crown liner are UPF 50+ sun-rated and an adjustable chinstrap and elasticized sweatband ensure a custom fit.

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