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.

Activewear
Activewear
45 products
Bottoms
Bottoms
126 products
Button Downs/Flannels
Button Downs/Flannels
94 products
Camouflage
Camouflage
156 products
Golf Shirts
Golf Shirts
55 products
Hats
Hats
245 products
Sun Shirts
Sun Shirts
28 products
Sweaters
Sweaters
1 product
Swimwear
Swimwear
30 products
T-Shirts
T-Shirts
368 products
Underwear
Underwear
10 products
Vest
Vest
7 products
Lounge Wear
Lounge Wear
4 products
Shorts
Shorts
54 products
Outerwear
Outerwear
55 products
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  • New
    Hemlock UPF 50+ Lifeguard Straw Hat - Monstera Hemlock UPF 50+ Lifeguard Straw Hat - Monstera
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    Hemlock Hats

    Hemlock UPF 50+ Lifeguard Straw Hat - Monstera

    Hemlock UPF 50+ Lifeguard Straw Hat - Monstera The perfect blend of FUNctional design and serious sun protection, Hemlock’s OG Lifeguard Hat features a tall cattleman crown, 4.5” wide brim, and certified UPF 50+ under-brim liner to shield...
    $39.99
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    Hemlock UPF 50+ Lifeguard Straw Hat - Hanalei Hula Hemlock UPF 50+ Lifeguard Straw Hat - Hanalei Hula
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    Hemlock Hats

    Hemlock UPF 50+ Lifeguard Straw Hat - Hanalei Hula

    Hemlock UPF 50+ Lifeguard Straw Hat - Hanalei Hula The perfect blend of FUNctional design and serious sun protection, Hemlock’s OG Lifeguard Hat features a tall cattleman crown, 4.5” wide brim, and certified UPF 50+ under-brim liner to shield...
    $39.99
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  • Chubbies The Bahamian Straw Hat Chubbies The Bahamian Straw Hat
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    Chubbies

    Chubbies The Bahamian Straw Hat

    Chubbies The Bahamian Straw Hat Like pineapples, shade, and straw hats? Well... then… chubbies has a business proposition for you... Fit & Design: One size fits most 17" in length 16" wide Crown height of 6.5" Headband circumference of...
    $34.50
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  • Chubbies Men's Big Bloomer Straw Hat Chubbies Men's Big Bloomer Straw Hat
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    Chubbies

    Chubbies Men's Big Bloomer Straw Hat

    Chubbies Men's Big Bloomer Straw Hat Wide Brim for Sun Protection Printed Underbrim Lining Lightweight & Breathable Adjustable Drawstring for Secure Fit Machine Washable Material: 100% Straw Lining: 100% Cotton Fit: One Size Fits Most Crown...
    $34.50
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  • Chubbies Men's Exploding Nacho Straw Hat Chubbies Men's Exploding Nacho Straw Hat
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    Chubbies

    Chubbies Men's Exploding Nacho Straw Hat

    Chubbies Men's Exploding Nacho Straw Hat Wide Brim for Sun Protection Printed Underbrim Lining Lightweight & Breathable Adjustable Drawstring for Secure Fit Machine Washable Tech Specs Material: 100% Straw Lining: 100% Cotton Fit: One Size...
    $34.50
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  • Chubbies The King of the Sea Straw Hat Chubbies The King of the Sea Straw Hat
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    Chubbies

    Chubbies The King of the Sea Straw Hat

    Chubbies The King of the Sea Straw Hat Vacation-style with built-in sun protection. Our straw hats feature a wide, sun-blocking brim lined with prints for a unique touch. The adjustable drawstring ensures a snug fit, even on windy days. Lightweight and...
    $34.50
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  • Chubbies The Mericas Classic Swim Trunk - 5.5" Chubbies The Mericas Classic Swim Trunk - 5.5"
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    Chubbies

    Chubbies The Mericas Classic Swim Trunk - 5.5"

    Chubbies The Mericas Classic Swim Trunk - 5.5" From sandy shores to scorching pool decks these ultra stretchy swimmers are here to make a splash. Featuring a quick-drying shell and your choice of liner, you’ll be comfortable no matter where the...
    $69.50
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  • Chubbies The Glades Beach Club Tee Chubbies The Glades Beach Club Tee
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    Chubbies

    Chubbies The Glades Beach Club Tee

    Chubbies The Glades Beach Club Tee The Non Pocket Graphic features bold colors to turn heads around town or at the beach. Made from super soft, premium material, you’ll love wearing this Chubbies shirt during warm temperatures. 60% Cotton 40%...
    $29.50
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  • Simply Southern Men's Seer Shorts - Reef Simply Southern Men's Seer Shorts - Reef
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    Simply Southern

    Simply Southern Men's Seer Shorts - Reef

    Simply Southern Men's Seer Shorts - Reef These men's seersucker shorts are the perfect short for going from beach to play. It features stylish and comfortable seersucker textured fabric with a elastic waistband and drawcord for ease of fit. Two front...
    $29.99
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  • Simply Southern Men's Seer Shorts - Blue Stripe
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    Simply Southern

    Simply Southern Men's Seer Shorts - Blue Stripe

    Simply Southern Men's Seer Shorts - Blue Stripe These men's seersucker shorts are the perfect short for going from beach to play. It features stylish and comfortable seersucker textured fabric with a elastic waistband and drawcord for ease of fit. Two...
    $29.99
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  • Simply Southern Men's Seer Shorts - Oyster
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    Simply Southern

    Simply Southern Men's Seer Shorts - Oyster

    Simply Southern Men's Seer Shorts - Oyster These men's seersucker shorts are the perfect short for going from beach to play. It features stylish and comfortable seersucker textured fabric with a elastic waistband and drawcord for ease of fit. Two front...
    $29.99
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  • Huk States 110 Trucker Hat - Naval Academy Huk States 110 Trucker Hat - Naval Academy
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    Huk

    Huk States 110 Trucker Hat - Naval Academy

    Huk States 110 Trucker Hat - Naval Academy This mid-profile trucker has a 3D graphic and a dark gray undervisor to decrease glare.  Additionally, it offers a moisture-wicking sweatband for comfortable wear. Designed in honor of our home state the...
    $29.99
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