Men's Underwear

Shop Simpson Outfitters for men’s underwear, offering a comfortable and supportive collection of briefs, boxers, and boxer briefs. Made with soft, breathable fabrics, our underwear is designed to keep you comfortable and dry all day long, providing the perfect fit for every man.

Men's Briefs & Boxers
Men's Briefs & Boxers
14 products
Men's Thermals
Men's Thermals
7 products
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  • Shinesty The Peppermint Pimp Canes Shinesty The Peppermint Pimp Canes
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    Shinesty

    Shinesty The Peppermint Pimp Canes

    Shinesty The Peppermint Pimp Canes Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is moisture wicking and breathable. All Modal is not equal. Our proprietary knitting process gives you a more sumptuous Modal per square inch for a softer, better...
    $29.99
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  • Shinesty The Nutty Soldier Shinesty The Nutty Soldier
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    Shinesty

    Shinesty The Nutty Soldier

    Shinesty The Nutty Soldier Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is moisture wicking and breathable. All Modal is not equal. Our proprietary knitting process gives you a more sumptuous Modal per square inch for a softer, better fitting,...
    $29.99
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  • Burlebo Men's 3-Pack Boxer Briefs Burlebo Men's 3-Pack Boxer Briefs
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    Burlebo

    Burlebo Men's 3-Pack Boxer Briefs

    Burlebo Men's 3-Pack Boxer Briefs Experience all-day comfort and bold seasonal style with the Boxer Briefs Collection. Designed with performance stretch fabric, these boxer briefs provide the perfect balance of flexibility, breathability, and...
    $59.99
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  • Shinesty Men's The Midnights Shinesty Men's The Midnights
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    Shinesty

    Shinesty Men's The Midnights

    Shinesty Men's The Midnights Your waist is now invisible...but the rest of you isn't. So now you look like a magicians-body-saw-trick just walking around. It's unnerving, and also exhilarating. Softest Fabric AroundLuxury 95% MicroModal, 5% Spandex is...
    $27.99
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  • Shinesty Men's The Mascot with Fly Shinesty Men's The Mascot with Fly
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    Shinesty

    Shinesty Men's The Mascot

    Shinesty Men's The Mascot with Fly Introducing The Mascot Ball Hammock® with fly, aka the eagle's nest, where your balls will experience an unprecedented level of comfort and support from here on out. It's as if your plums mounted a cloud while...
    $27.99
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  • Shinesty Men's The Front Nine Shinesty Men's The Front Nine
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    Shinesty

    Shinesty Men's The Front Nine

    Shinesty Men's The Front Nine Hit the links in this golf themed Ball Hammock® Pouch Underwear, featuring your own personal caddy to look after your balls. Because unlike in golf, you really don’t want to get a hole in one. Softest Fabric...
    $27.99
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  • Saxx Vibe Xtra Soft Comfort 6" Boxer Brief - Black Saxx Vibe Xtra Soft Comfort 6" Boxer Brief - Dark Navy Heather
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    Saxx Underwear Co.

    Saxx Vibe Xtra Soft Comfort 6" Boxer Brief

    Saxx Vibe Xtra Soft Comfort 6" Boxer Brief Feel good vibes in best-selling, Vibe Xtra Soft Comfort Boxer Briefs with Stop Drop Technology™ — a barely-there wicking structure built into the BallPark Pouch® — feature No-RideUp...
    $20.00 - $29.99
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  • Free Fly Men's Bamboo Boxer Brief - Vintage Camo Free Fly Men's Bamboo Boxer Brief - Vintage Camo
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    Free Fly Apparel

    Free Fly Men's Bamboo Motion Boxer Brief

    Free Fly Men's Bamboo Motion Boxer Brief Ready for a top drawer refresh? Our Bamboo Motion Boxer Brief is here to replace all your old pairs with an insanely soft, four-way stretch design. Outfitted with natural odor-resistance, they’ll keep you...
    $32.99
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  • Indera Men's 2 Layer Merino Performance Crew Grey
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    Indera Mills

    Indera Men's 2 Layer Merino Performance Crew Grey

    Indera Men's 2 Layer Merino Performance Crew Grey 2-Layer fabric construction helps trap and retain body heat Fabric Weight: 7.0 oz Fiber Content Outside Layer: 70% Polyester / 30% Merino Wool Inside Layer: 100% Performance Polyester formulated...
    $24.99 - $27.99
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  • Indera Men's 2 Layer Merino Performance Pant Grey
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    Indera Mills

    Indera Men's 2 Layer Merino Performance Pant Grey

    Indera Men's 2 Layer Merino Performance Pant Grey 2-Layer fabric construction helps trap and retain body heat Fabric Weight: 7.0 oz Fiber Content Outside Layer: 70% Polyester / 30% Merino Wool Inside Layer: 100% Performance Polyester formulated...
    $24.99 - $27.99
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  • Indera Men's Traditional Waffle Crew Natural
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    Indera Mills

    Indera Men's Traditional Waffle Crew Natural

    Indera Men's Traditional Waffle Crew  Natural Waffle knit fabric traps and retains body heat using the fabric texture Fabric Weight: 5.0 oz Fiber Content: 65% Cotton / 35% Polyester Crew neck Set-in long sleeves Rib collar and cuffs help keep the...
    $7.99 - $9.99
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  • Indera Men's Traditional Waffle Pant Natural
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    Indera Mills

    Indera Men's Traditional Waffle Pant Natural

    Indera Men's Traditional Waffle Pant  Natural Waffle knit fabric traps and retains body heat using the fabric texture Fabric Weight: 5.0 oz Fiber Content: 65% Cotton / 35% Polyester Ankle length Functioning front fly Center back gusset Rib cuffs...
    $7.99 - $9.99
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  • Indera Men's Unionsuit-Red
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    Indera Mills

    Indera Men's Unionsuit

    Indera Men's Unionsuit 100% Cotton Thermals Smooth 1×1 rib knit Full cut one-piece for comfort Full button front with one-button vertical flap seat Rated for cold temperatures
    $32.99
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  • Saxx Ultra Soft BB Fly-Horizon Stripe Navy
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    Saxx Underwear Co.

    Saxx Ultra Soft BB Fly

    Saxx Ultra Soft BB Fly Featuring a Relaxed fit for unrestrictive moment, this men's camo underwear is form-fitting through the butt and thighs, with extra ease at the leg opening. Men who prefer their underwear with a fly will be happy to see this...
    $20.00 - $29.99
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