
Top steep and cheap Deals & Price Drops for May 2026
Explore verified steep and cheap discounts and price drops updated in the last 30 days.
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Brixton Jo Straw Rancher Hat in Natural / Beige - ...
With a wide 4-inch brim and fine Tripilla straw, Brixton's Jo Straw Rancher Hat delivers plenty of sun protection and style that's appropriate for town as well as the ranch.
$98.95
$39.5860% OFF
DAKINE All Day Trucker Hat in Grey / Dark Tide
If youre looking for a classic trucker hat that fits in everywherefrom the beach to the bar to the grocery storethe All Day Trucker ticks all the boxes. Imbued with a classy elegance, the foam-backed, 5-panel cap features a slightly curved bill adorned with our unique Dark Tide print on the underside. The adjustable snap back enables you to dial in the perfect fit, while the woven logo patch and understated rope detail on the front provide a refined contrast to the grey/dark tide colorway combo. Youll be holding your head high all day long.
$28.00
$11.2060% OFF
La Sportiva Women's Terry Beanie in Redwood / Chal...
When the cold bites, the Women's Terry Beanie keeps us feeling cozy and looking stylish. The chunky knit design traps warmth while adding classic texture to our winter wardrobe, whether we're strolling downtown or heading up the hill. Made from soft, synthetic fabric, it feels comfortable against our skin, and the fun pom-pom on top gives a nod to carefree winter days. Lightweight and easy to pack, it's our go-to for everyday adventures when warmth and style are both a must.
$35.00
$14.7058% OFF
Buff Merino Active Beanie in Solid Black
What Our Gearhead® Experts Are Saying: "This is the beanie I grab for chilly dawn runs or evening dog walks. The merino blend keeps my temperature steady, never too hot or too cold, and the reflectivity is super noticeable in low light. Soft, relaxed, and surprisingly performance-driven—it’s a great blend of casual comfort and technical function." We love how the Buff Merino Active Beanie takes laid-back style and quietly layers in real performance. With more than half its fibers made from ethically sourced merino wool, it naturally regulates temperature, wicks moisture, and resists odor—making it just as ready for pre-work run sessions as it is for weekends spent exploring town. The relaxed fit and turn-up cuff give it an easy, everyday feel, while subtle 360° reflectivity helps keep us visible when we’re out before sunrise or long after dusk. Its Polycolon blend enhances durability and quick-drying performance, ensuring the beanie stays comfortable through changing weather and high-output activity. Whether we’re moving fast, wandering slow, or simply staying warm on a chill night, the Merino Active Beanie keeps us prepared, comfortable, and confidently seen.
$54.00
$22.6858% OFF
Mountain Hardwear Since 93 Foam Trucker Hat in Ste...
What Our Gearhead® Experts Are Saying:"I love a good trucker hat, and the Since 93 Foam Trucker Hat is my go-to for everyday wear. The structured crown and curved brim give it that classic look, while the breathable mesh back keeps me cool. Plus, the Bureo brim made from recycled fishing nets adds a sustainable touch I really appreciate."The Since 93 Foam Trucker Hat brings classic trucker style with a sustainable twist. Designed with a structured cotton twill front and a breathable mesh back, it delivers the ideal balance of comfort and durability. The curved brim shields our eyes from the sun, while the adjustable snapback ensures the perfect fit for any adventure. What sets this hat apart is its eco-conscious construction—featuring a Bureo brim made from recycled fishing nets and recycled trims throughout. Whether we're hitting the trail, setting up camp, or just keeping it casual, this trucker hat is a staple for any outdoor lifestyle.
$34.99
$14.7058% OFF
Mountain Hardwear Recycled Trucker Hat in Hardwear...
What Our Gearhead® Experts Are Saying:"This hat does it all—looks good, breathes well, and has one of the most impressive recycled builds I’ve seen. The brim made from fishing nets is a cool detail, and the fit is just right for all-day wear on the trail or in town."From summit hikes to weekend road trips, the Mountain Hardwear Recycled Trucker Hat is our go-to for breathable coverage and eco-conscious style. Built entirely from recycled materials—including the mesh, the thread, and even the Bureo brim and snap made from reclaimed fishing nets—this hat makes a big impact with a minimal footprint. Its mid-rise trucker shape with a structured crown and curved brim gives us a classic fit that stays put and looks sharp whether we’re on the move or posted up by the campfire. Lightweight, breathable, and built with purpose, the Recycled Trucker Hat is made for those who play hard and tread lightly.
$34.99
$14.7058% OFF
Backcountry Est. 96 Trucker Hat in Black
What Our Gearhead® Experts Are Saying:"Our Backcountry Est. 96 Trucker Hat features a retro-inspired patch reminiscent of our public lands and proud of our heritage."We throw on the Est. 96 Trucker Hat when the plan is loose and the day could go anywhere. The structured front and curved brim give it that familiar trucker feel, while the mesh back keeps things breathable when the sun’s out. A cotton-blend front panel delivers a softer, more natural feel against your forehead, while the snapback closure makes dialing in the fit quick and easy. Finished with an oversized heritage patch, the Est. 96 Trucker Hat keeps things simple, comfortable, and ready for whatever the day turns into.
$29.00
$13.0555% OFF
TravisMathew Hidden Agenda Hat in Captains Blue
What Our Gearhead® Experts Are Saying:"This is the kind of snapback I toss on when I need to pull a look together without trying too hard. It’s structured but still relaxed, and the low-key branding keeps it clean."Whether we're heading out for coffee or catching golden hour on the coast, the Hidden Agenda Hat brings effortless style to our day. TravisMathew delivers this semi-structured snapback in a rich Captain Blue shade with minimalist embroidered branding, offering a laid-back yet polished look that pairs with anything. With its soft fabric construction and adjustable snapback fit, it’s made for easy wear on the trail, in town, or anywhere in between. It’s the kind of hat we reach for again and again—simple, versatile, and subtly bold.
$39.95
$17.9855% OFF
Brixton Women's Running On Empty NP LP Adjustable ...
What Our Gearhead® Experts Are Saying: "This is my go-to everyday hat. It’s super lightweight, low-profile, and the moisture-wicking sweatband is a subtle but major plus. The embroidered front and soft cotton blend give it a relaxed vibe, and the NetPlus visor makes it feel like you're doing something good with your gear." We throw on the Brixton Running On Empty NP LP Adjustable Hat when we want that perfect, lived-in feel with a side of conscious construction. With its low-profile, unstructured design and soft cotton-blend fabric, this dad hat brings laid-back style to road trips, trailhead hangs, and everyday wear. It’s the kind of hat that feels like a favorite from day one. The Bureo NetPlus visor is made from recycled fishing nets, helping reduce plastic waste while keeping the sun out of our eyes. A moisture-wicking sweatband keeps us cool when temps rise, and the adjustable strapback ensures a custom fit. Finished with direct embroidery and a light rinse wash, the Running On Empty hat looks good, feels great, and fits in just about anywhere.
$29.95
$13.4855% OFF
Castelli Women's Light Head Thingy in Violet Mist ...
100% polyester jersey for maximum moisture managementSeamless continuous-tube constructionSublimated graphicSummer weight
$29.99
$13.5055% OFF
Backcountry Est. 96 Flow Hat in Black
What Our Gearhead® Experts Are Saying:"The Est. 96 Flow Hat is my favorite for multi-sport days. The cotton twill is light and breathable, and the snapback makes it easy to adjust on the fly."We grab the Backcountry Est. 96 Flow Hat when our day takes us from the skin track to the crag. Backcountry's heritage embroidery and classic 5-panel design keep our look timeless, while the cotton twill construction ensures lightweight comfort and breathability. The adjustable snapback closure means a perfect fit, whether we're chasing summits or city sunsets.
$29.00
$14.5050% OFF
GOREWEAR Essence Light Headband in Black / Lab Gra...
What Our Gearhead® Experts Are Saying: "This headband is a staple on chilly trail runs and rides. It’s light enough to fit comfortably under a helmet but warm enough to take the edge off early morning wind. It doesn’t shift or bunch up either, which is key when I’m on the move."We reach for the Gore Wear Essence Light Headband when we need lightweight warmth without the bulk. Designed to perform through the shoulder seasons and high-output workouts, this stretchy, breathable headband keeps our ears warm without overheating. Whether layered under a helmet or worn solo on breezy runs, it stays put and stays comfortable. Gore’s ergonomic design contours to our head for a secure fit that resists bunching or sliding, even through high movement. With just the right amount of insulation and weightless coverage, the Essence Light Headband keeps us focused on the trail ahead—not the temperature.
$25.00
$12.5050% OFF
Castelli Pro Thermal Neck Warmer in Belgian Blue
What Our Gearhead® Experts Are Saying:"The Pro Thermal Neck Warmer is my go-to for cold rides. The Thermoflex fabric is soft and super warm, while the raw-cut edges keep it low-profile under my jacket. I love that I can easily use it as a neck warmer, headband, or even a cap. It’s essential for those chilly days."The Castelli Pro Thermal Neck Warmer is the ultimate cold-weather accessory, designed to keep us warm without adding extra bulk. Made from soft, stretchy Thermoflex fabric, this neck warmer offers excellent insulation while remaining comfortable against the skin. Its versatile design lets us wear it as a neck warmer, bandana, or cap, adapting to changing conditions and needs on any ride. The flat-lock stitching and raw-cut edge provide a seamless fit, making it easy to layer under jackets without any added bulk. Whether we’re facing early-morning chills or windy descents, this neck warmer is a reliable piece for every ride.
$25.00
$12.5050% OFF
DAKINE Traveler Trucker Hat in Hawaii
Planes, trains, automobiles, and boats: Whatever your adventure demands, the Traveler Trucker is ready for the long haul. Featuring a roomy, high-crown fit with a foam-backed front ripstop panel, this flat-billed hat has a mesh interior sweatband, an adjustable snap back, and mesh polyester back panels that will keep the air flowing while you’re on the move. And with a printed graphic and a brim made of Bureo’s NetPlus material—which is 100% sourced from recycled fishing nets—you can look smart and reduce your impact at the same time.
$30.00
$15.0050% OFF
Smartwool Patch Beanie - Kids' in Black - Size: L/...
We’re keeping the heads of our little adventure buddies warm with the Smartwool Patch Beanie. Made with Merino wool, the beanie wicks moisture and resists odors so they can wear it comfortably on the playground and on a hike or two between washes. In addition to the wool, the beanie features durable recycled polyester yarns so the beanie can go anywhere they do with confidence.
$30.00
$15.0050% OFF
Smartwool Merino 250 Reversible Pattern Cuffed Bea...
Winter warmth begins with socks on the feet and a hat on the head, for that's where you'll lose heat fast if either are bare. Teach your youngin' this early on with the Kids' SmartWool Merino 250 Reversible Pattern Cuffed Beanie and you'll be setting them on a path to success. The heavyweight strength wool will make for whine-free mornings even on the colder days, and the low-profile seams mean this hat can be comfortably worn under their helmet.
$32.00
$16.0050% OFF
GOREWEAR C3 GORE Windstopper Helmet Cap in White /...
Your helmet is great in the summer, with plenty of vents to keep air moving to keep your head cool. However, when temperatures start to drop, you need to add the Gore Wear C3 Gore Winstopper Helmet Cap to your combination to keep yourself warm. This hat features a Gore Windstopper membrane to defend your head against heat loss without trapping air in—keeping you from overheating. The synthetic interior efficiently wicks away moisture, so no matter how hard you pedal you can expect to stay dry, while an elastic binding keeps the stretchy fabric from moving around.
$45.00
$22.5050% OFF
Brixton Laredo Branded Cowboy Hat in Antique Bronz...
Backcountry Gearhead Recommendation "The Laredo is my go-to when I want sun protection with a bit of style. It’s well-shaped, holds up to wear, and the moisture-wicking band keeps it comfortable all day. Plus, the adjustable fit means I don’t have to worry about wind or long days outside." With timeless Western character and modern comfort, the Brixton Laredo Branded Cowboy Hat rides the line between rugged function and everyday style. Crafted from 100% wool felt and shaped with a traditional cattleman crown and side roll brim, it’s made to stand out whether you're at the rodeo or on the ranch. An internal Velcro strap ensures a dialed-in fit, while the moisture-wicking sweatband keeps things breathable when the sun beats down. Finished with a double-wrapped leather band and metal logo plaque, the Laredo blends frontier grit with refined polish.
$128.95
$64.4850% OFF
Brixton Laredo Branded Cowboy Hat in Antique Bronz...
Backcountry Gearhead Recommendation "The Laredo is my go-to when I want sun protection with a bit of style. It’s well-shaped, holds up to wear, and the moisture-wicking band keeps it comfortable all day. Plus, the adjustable fit means I don’t have to worry about wind or long days outside." With timeless Western character and modern comfort, the Brixton Laredo Branded Cowboy Hat rides the line between rugged function and everyday style. Crafted from 100% wool felt and shaped with a traditional cattleman crown and side roll brim, it’s made to stand out whether you're at the rodeo or on the ranch. An internal Velcro strap ensures a dialed-in fit, while the moisture-wicking sweatband keeps things breathable when the sun beats down. Finished with a double-wrapped leather band and metal logo plaque, the Laredo blends frontier grit with refined polish.
$128.95
$64.4850% OFF
Katin Splash Hat in Black
What Our Gearhead® Experts Are Saying:"The Splash Hat is one of my go-tos for warm weather—it’s super light, dries quickly, and the mid-crown fit is just right. The recycled nylon makes it a feel-good choice, and the custom embroidery gives it a clean, beach-ready look. Great for hikes, paddling, or just hanging out in the sun."Made for sun-soaked days on the water or trail, the Katin Splash Hat delivers everyday comfort with eco-conscious construction. This lightweight 5-panel cap is built from 100% recycled nylon for a breathable, quick-drying feel that stands up to sweat, splashes, and summer heat. The mid-crown, unstructured design gives it a relaxed fit that packs easily for travel or outdoor adventures, while the adjustable snapback closure ensures a dialed-in feel. Finished with custom Katin embroidery, the Splash Hat pairs coastal vibes with all-purpose utility for wherever the day takes us.
$28.95
$14.4850% OFF
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