Sunday Afternoons Woodland Trucker

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

Sun worshippers beware—the Sun Guardian Hat has arrived! Made from 100% natural straw, this classic lifeguard hat has been given a serious upgrade: a UPF 50+ brim and top-of-crown liner, an elasticized sweatband for a custom fit, a dark underbrim to reduce glare, an adjustable and technical chinstrap for when the wind picks up, and custom artwork by Carlos del Rio on the crown patch for a special touch. Ideal for outdoor enthusiasts who work and play in full sun.

by Sunday Afternoons · Ashland, Oregon

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

Offering UPF 50+ sun protection and made from bluesign® fabric, the Sunward Radar is a perfect choice, whether you're trekking, traveling, or training. This hat features a wicking sweatband and stretch-comfort adjustable sizing, so it fits just right. The curved brim is structured, offering premium shade and subtle reflective details that are handy in low light.

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

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

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

Whether you’re working at home or strolling downtown, the Montana Hat fills the need for an every day warm, comfortable and UPF 50+ wool felt hat. The Montana is the perfect 3-season hat for sun protection. High quality 100% wool felt maintains shape even after packing.

by Sunday Afternoons · Ashland, Oregon

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

Ready for sunny adventures far away or close to home, the Wanderlust Fedora is a playful take on a classic style. Offering UPF 50+ sun protection and a decorative, beaded hatband, this hat is made from breathable poly/paper braid. The bluesign® sweatband and internal adjustable sizing offer comfort and a custom fit.

by Sunday Afternoons · Ashland, Oregon

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

This cap features a classic, six-panel construction and a cool, metal/leatherette logo badge. The Melton wool blend adds warmth and style to your favorite look. With adjustable sizing, wicking sweatband, and a 2 ¾" brim for UPF 50+ sun protection. Features & Specs UPF 50+ sun rating 2¾" (7cm) brim Melton wool blend Wicking sweatband Adjustable sizing Weight: 3.5 ounces/102…

by Sunday Afternoons · Ashland, Oregon

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

Add some flair to your winter wardrobe with the UPF 50+ Avalon Bucket. The low-profile, downsloping brim and cozy yet breathable textured weave make this hat a great choice when the sun peeks out through the clouds. The wicking sweatband and internal adjustable sizing make for a comfortable, custom fit, and a decorative hatband adds simple, understated beauty.

by Sunday Afternoons · Ashland, Oregon

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

Add some flair to your winter wardrobe with the UPF 50+ Avalon Bucket. The low-profile, downsloping brim and cozy yet breathable textured weave make this hat a great choice when the sun peeks out through the clouds. The wicking sweatband and internal adjustable sizing make for a comfortable, custom fit, and a decorative hatband adds simple, understated beauty.

by Sunday Afternoons · Ashland, Oregon

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

Stitched with reflective fiber woven into the yarn, the Kids’ Nightfall Reflective Beanie features a fun heathered pattern by day and reflects with a little flash and flair when the sun goes down. Reversible with a fitted crown for a snug fit, this beanie is made from ultra-soft acrylic knit so kids stay cozy and comfortable on every adventure.

by Sunday Afternoons · Ashland, Oregon

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

Add some flair to your winter wardrobe with the UPF 50+ Avalon Bucket. The low-profile, downsloping brim and cozy yet breathable textured weave make this hat a great choice when the sun peeks out through the clouds. The wicking sweatband and internal adjustable sizing make for a comfortable, custom fit, and a decorative hatband adds simple, understated beauty.

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 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

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

Simplicity defined for all your warm weather explorations. This lightweight marvel is a master moisture manager with both strategic ventilation and a wicking sweatband. When you seek relief near the water, you can relax knowing your Cruiser will float should it get away from you. This is a hat you won’t forget time and time again.

by Sunday Afternoons · Ashland, Oregon

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

At last all the features you love in a fun-sized trucker! The Kids™ Feel Good Trucker Series showcases embroidered patches in many outdoor-inspired designs. With modern technical features, such as 100% recycled, bluesign® fabric and a PFAS-free durable water repellent finish, kids will stay cool, shaded, and dry. The wicking sweatband and mesh ventilation, plus StretchBack Sizing, offer comfort and a great fit as kids grow.

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

Whether you’re strolling amongst the grapevines of your region’s vineyards or the ones in your own backyard garden, the Vineyard Hat takes you there. The fun, upturned kettle brim flatters everyone. Beaded hatband adjusts to fit just for you. Soft, packable fabric ribbon construction means you can toss it into your suitcase and wear it wine tasting abroad.

by Sunday Afternoons · Ashland, Oregon

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

Cold temps won’t cramp your style when you’re rocking the Alpine Tundra Cap. The warmth stays in with Cross Core™ Aerogel insulation while the cozy flannel liner keeps you toasty. The BreezeBlocker™ windproof ear flaps on this low profile, approachable ball cap can be folded up and away when temps rise. Made from recycled content and PFAS-durable water repellent finish this warm cap is also rated UPF 50+.

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

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