Sunday Afternoons Dream Seeker Cooling 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

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

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

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

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

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

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

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

Featuring a magical design by artist Acacia Lacy, the Whale Song 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.

by Sunday Afternoons · Ashland, Oregon

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

Local artist Acacia Lacy’s love of the outdoors shines through on our new take on the classic trucker, and the Rainbow Trout Trucker is no exception. A deep brim offers the perfect shade, and our comfy and strategic design makes this cap the perfect choice for kids on the go all year long. Features & Specs 2 ½" Brim Limited Edition Artwork Strategic Crown Ventilation Wicking Sweatband Adjustable Sizing Weight: 2.2…

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

There’s a chill in the air, which can only mean one thing—it’s sweater weather and time for a cozy new hat! The Camden Hat adds a funky flair to your winter wardrobe with a textured weave that breathes just right. With the UPF 50+ sun rating you can count on even as the days get shorter, this fun fedora is long on style. Internal adjustable sizing and 2 ½” brim.

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

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

“This hat with UPF 50+ fabric is so airy and lightweight, you could easily forget you’re wearing it, which means you’re more likely to leave it on your head.” — Wirecutter Hear that? It’s the call of the wild—don’t forget your Ultra Adventure Hat! The Ultra Adventure Hat is updated with a slimmer silhouette and fun technical details like our Reverse Split Brim™ and Sunglass Lock™, but still retains the sun protection, ventilation, and moisture management of our iconic Adventure Hat. Also available in 100% waterproof version - Ultra Adventure Storm .

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

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

From countryside to cityscapes, the Tessa transitions seamlessly. We’ve updated the on-trend fedora silhouette with a slightly floppy brim and soft wool felt that provides comfortable warmth and easy packability. The internal sizing system ensures a dreamy fit. Dresses up with long skirts and boots, dresses down with puffy vests and…

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

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

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

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