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.

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7 products
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  • Heybo Performance Boxers: Evterra Skinnywater
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    HeyBo

    Heybo Performance Boxers: Evterra Skinnywater

    Heybo Performance Boxers: Evterra Skinnywater At Heybo Outdoors, we didn't want to make just another pair of boxers - we wanted to make your favorite. We gave ours a classic cut, labeled the waistband, and crafted a moisture wicking fabric that will...
    $24.99
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  • Heybo Outdoors Performance Boxers Pointer Heybo Outdoors Performance Boxers Pointer
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    HeyBo

    Heybo Outdoors Performance Boxers Pointer

    At Heybo Outdoors, we didn't want to make just another pair of boxers - we wanted to make your favorite. We gave ours a classic cut, labeled the waistband, and crafted a moisture wicking fabric that will keep you dry in all you do...
    $24.99
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  • Saxx Men's Multi-Sport Mesh 2 Pack - Palm Camo Glow/Black
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    Saxx Underwear Co.

    Saxx Men's Multi-Sport Mesh 2 Pack

    Saxx Men's Multi-Sport Mesh 2 Pack All-new Multi-Sport Mesh, featuring a NO-RIDEUP LEG™, Stop Drop Technology™, and the BallPark Pouch® PRO, is a soft and versatile Performance style that keeps everything put, and dry, during sport and...
    $39.99
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  • Saxx Men's Multi-Sport Mesh Boxer Brief - Remote Camo - Faded Black Saxx Men's Multi-Sport Mesh Boxer Brief - Remote Camo - Faded Black
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    Saxx Underwear Co.

    Saxx Men's Multi-Sport Mesh Boxer Brief

    Saxx Men's Multi-Sport Mesh Boxer Brief All-new Multi-Sport Mesh, featuring a NO-RIDEUP LEG™, Stop Drop Technology™, and the BallPark Pouch® PRO, is a soft and versatile Performance style that keeps everything put, and dry, during sport...
    $24.99
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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 Quest Quick Dry Mesh Boxer Brief-Dark Charcoal II SAXX Quest Quick Dry Mesh Boxer Brief-Dark Charcoal II
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    Saxx Underwear Co.

    SAXX Quest Quick Dry Mesh Boxer Brief

    SAXX Quest Quick Dry Mesh Boxer Brief How It Fits Slim Fit: form-fitting around the butt and thighs. Features a fly for easy access. Made For The guy who's going places. Made using a quick-dry mesh, Quest holds its own on any outdoor adventure, while...
    $20.00 - $29.99
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  • Saxx Ultra Soft BB Fly-Horizon Stripe Navy Saxx Ultra Soft BB Fly-Beers of the World
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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...
    $29.99
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