Sunday Afternoons Midnight Mountain Trucker - SALE

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

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

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

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

With sun-bleached color and outdoorsy graphics, the women's Valley Girl trucker hat sets the tone for wanderlust. The laid-back style and earthy tones demand nothing more than grab-and-go planning for off-hours adventure. It's unlined and has a mesh back for an airy, breezy feel.

by Pistil · Portland, Oregon

🚚 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

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 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

Local artist Acacia Lacy’s limited edition artwork featuring glow in the dark moon and stars are sure to make the Kids’ Lone Wolf Trucker everyone’s new favorite hat. With classic trucker mesh ventilation, wicking sweatband, adjustable sizing, and a comfortable fit, this trucker makes heading outside even more fun in any kind of weather.

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

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

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

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

As seen in Seriously though…what can we say? This is adorable sun protection at its best. A mini version of our best-selling Kids’ Play Hat, the super soft fabrics and construction keep your little-little ones comfy and shaded from the sun. Designed with an infant’s needs in mind, this hat packs up in a diaper bag, transitions easily to a stroller with no back brim to get in the way, washes up like a breeze, and adjusts with baby’s growing head. The easy chinstrap ensures zero fuss with putting it on or taking it off.

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

“If you’re spending hours on your summer garden project or just need some extra coverage for your face and neck while kayaking, the Sunday Afternoons Adventure Hat is a superb choice thanks to its extra-long brim and neck cape. This full-coverage option stands out from the rest thanks to its functional design.” — Gear Junkie This is it—the most recognizable sun hat on the planet! You may not see it on a Parisian runway, but you’ve seen this Sunday Afternoons original on adventurers everywhere who know how to have a good time in the elements without losing their cool.

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

Made from sustainably sourced Everwool™ 100% extra fine merino wool from humanely raised, non-mulesed sheep, you’ll look as good as you feel in the Outback Merino Beanie. With an ombre stripe, flecked pattern, and a cozy microfleece earband for softness, the insulative value of this cap will keep you snug and warm in any kind of weather.

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.

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

Ladies, we know you like options, so we’ve designed our reversible Clear Creek Boonie to give you two looks in one! Take one side out for a ramble through the wilderness, then flip it over when you get to the café—both sides feature high performance fabrics that look and feel great. The adjustable cordlock dials in your custom, comfy fit. The chinstrap holds it close when you’re on the move but detaches when it’s time to kick back. Going somewhere? The Clear Creek packs completely flat with your travel itinerary.

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

Not all who wander are lost, but we recommend they take a hat on their journeys. The Brushline’s timeless design hits all the marks: lightweight, sun protective, breathable, water and stain resistant. The adjustable sizing system features some stretch for all-day wearability, and there’s a nifty spot to hold your sunglasses. It’s a good thing the Brushline packs up quick and easy, because you never know where your trails may go!

by Sunday Afternoons · Ashland, Oregon

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