Men's Apparel

Shop men's apparel at Simpson Outfitters for durable and stylish clothing designed for outdoor adventures. From performance jackets and hiking pants to casual wear, our collection combines comfort and functionality, ensuring you’re equipped for any outdoor activity, season after season.

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  • Duck Head 5" Gold School Chino Short - Stone Duck Head 5" Gold School Chino Short - Stone

    Duck Head

    Duck Head 5" Gold School Chino Short

    Duck Head 5" Gold School Chino Short The Duck Head Gold School Short shares every detail with our full-length chino. Same signature button, same drill cloth interior, and same 7.5 oz. cotton twill with a trace of functional stretch. The 5” inseam...
    $64.99
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    Marsh Wear Tide Rider Hat - Charcoal Marsh Wear Tide Rider Hat - Charcoal
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    Marsh Wear

    Marsh Wear Tide Rider Hat - Charcoal

    Marsh Wear Tide Rider Hat - Charcoal 5 Panel Unstructured Hat Polyester crown with foam visor, laser cut venting Screenprint logo at crown Mid profile fit Snapback
    Was: $38.99
    $33.14
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    Southern Tide Driver Knot Too Bad Polo Southern Tide Driver Knot Too Bad Polo

    Southern Tide

    Southern Tide Driver Knot Too Bad Polo

    Southern Tide Driver Knot Too Bad Polo Look polished and put together with the Driver Knot Too Bad Polo Shirt. Modern prints and a classic cut make this polo shirt an important spring or summer staple, while performance fabric and a drop-tail hem keep...
    Was: $84.99
    $67.99
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    Duck Head Long Drive Performance Polo - Marine Blue Duck Head Long Drive Performance Polo - Marine Blue

    Duck Head

    Duck Head Long Drive Performance Polo

    Duck Head Long Drive Performance Polo Elevate your game with the Long Drive Performance Polo. Crafted from vibrant striped and printed jersey, it combines style with performance, featuring moisture-wicking, odor resistance, and quick-dry technology to...
    Was: $79.99
    $63.99
  • Duck Head Men's Performance Poplin Sport Shirt - Sunwashed Red Duck Head Men's Performance Poplin Sport Shirt - Sunwashed Red

    Duck Head

    Duck Head Men's Performance Poplin Sport Shirt

    Duck Head Men's Performance Poplin Sport Shirt Introducing our most comfortable performance button-downs yet. We managed to make our performance fabric even softer by utilizing rayon from bamboo. This lightweight shirt is a testament to the versatility...
    $99.99
  • Free Fly Men's Reverb Short - Woodland Camo Free Fly Men's Reverb Short - Woodland Camo

    Free Fly Apparel

    Free Fly Men's Reverb Short - Woodland Camo

    Free Fly Men's Reverb Short - Woodland Camo The Reverb Short is a jack-of-all-trades performance short, designed to handle whatever your day has in store. Part athletic short, swim short, and casual everyday short—it’s 100% ready to tackle...
    $73.99
  • Free Fly Men's Breeze Short - 8" - Legion Blue Free Fly Men's Breeze Short - 8" - Legion Blue

    Free Fly Apparel

    Free Fly Men's Breeze Short - 8"

    Free Fly Men's Breeze Short - 8" Light, airy, and packed with stretch, our Breeze Collection delivers performance-level comfort and casual, everyday style. The Breeze Short has been a bestseller ever since we first designed it almost 10 years ago, thanks...
    $67.99
  • Free Fly Men's Breeze Short - 6" - Dusk Blue II Free Fly Men's Breeze Short - 6" - Dusk Blue II

    Free Fly Apparel

    Free Fly Men's Breeze Short - 6"

    Free Fly Men's Breeze Short - 6" Light, airy, and packed with stretch, our Breeze Collection delivers performance-level comfort and casual, everyday style. The Breeze Short has been a bestseller ever since we first designed it almost 10 years ago, thanks...
    $67.99
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    Free Fly Adventure Outfitters Mesh Hat - Vintage Camo Free Fly Adventure Outfitters Mesh Hat - Vintage Camo
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    Free Fly Apparel

    Free Fly Adventure Outfitters Mesh Hat - Vintage Camo

    Free Fly Adventure Outfitters Mesh Hat - Vintage Camo The sun sinks into the sea. A couple palm trees gently sway in the warm breeze. Even if you’re not going on vacation any time soon, you can channel tropical vibes wherever you are in the...
    Was: $33.99
    $28.89
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  • Simply Southern Men's Lab Tee - Washed Charcoal Simply Southern Men's Lab Tee - Washed Charcoal

    Simply Southern

    Simply Southern Men's Lab Tee - Washed Charcoal

    Simply Southern Men's Lab Tee - Washed Charcoal Mineral washed coal short sleeve shirt with the phrase 'Just a good ol' 'merican dude' and a dog with a cigar, shades, and hat. Simply Southern logo below and on left chest. 100% cotton. Unisex sizing...
    $18.99 - $20.99
  • Simply Southern Men's Mallard Tee - Khaki Simply Southern Men's Mallard Tee - Khaki

    Simply Southern

    Simply Southern Men's Mallard Tee - Khaki

    Simply Southern Men's Mallard Tee - Khaki Khaki short sleeve shirt with a mallard in water and Simply Southern logo below.Simply Southern logo with dog holding leash in mouth on left chest. 100% cotton. Unisex sizing.  
    $16.99 - $18.99
  • Simply Southern Men's Camo Logo Tee - Khaki Simply Southern Men's Camo Logo Tee - Khaki

    Simply Southern

    Simply Southern Men's Camo Logo Tee - Khaki

    Simply Southern Men's Camo Logo Tee - Khaki Khaki short sleeve shirt with a large camouflage patch with phrase ''Merican dude' and Simply Southern logo below.Simply Southern logo with dog holding leash in mouth on left chest. 100% cotton. Unisex sizing...
    $16.99 - $18.99
  • Simply Southern Men's Bass Tee - Star Simply Southern Men's Bass Tee - Star

    Simply Southern

    Simply Southern Men's Bass Tee - Star

    Simply Southern Men's Bass Tee - Star Light gray short sleeve with the phrase 'Just a good ol' 'merican dude' and a large bass and mountains in the background. Simply Southern logo below. Simply Southern logo with dog holding leash in mouth on left chest...
    $16.99 - $18.99