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
43 products
Bottoms
Bottoms
115 products
Button Downs/Flannels
Button Downs/Flannels
81 products
Camouflage
Camouflage
162 products
Golf Shirts
Golf Shirts
50 products
Hats
Hats
258 products
Sun Shirts
Sun Shirts
28 products
Sweaters
Sweaters
1 product
Swimwear
Swimwear
29 products
T-Shirts
T-Shirts
322 products
Underwear
Underwear
8 products
Vest
Vest
7 products
Lounge Wear
Lounge Wear
3 products
Shorts
Shorts
55 products
Outerwear
Outerwear
39 products
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  • Southern Tide ST Palmetto Trucker Hat Southern Tide ST Palmetto Trucker Hat
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    Southern Tide

    Southern Tide ST Palmetto Trucker Hat

    Southern Tide ST Palmetto Trucker Hat Embrace the essence of coastal living this spring with the Palmetto Trucker Hat. Perfect for sunny days and outdoor adventures, this grey hat combines classic style with elevated comfort, making it an essential...
    $29.99
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  • Southern Tide Petal Party Boxer Southern Tide Petal Party Boxer
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    Southern Tide

    Southern Tide Petal Party Boxer

    Southern Tide Petal Party Boxer Crafted from a premium blend, these boxers provide ultimate comfort and breathability, ensuring you feel great all day long. The playful Petal Party print adds a fun, colorful touch, making these men's boxers a standout...
    $27.99
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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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  • Hari Mari Sun Wave Unisex Snapback Hat - White Hari Mari Sun Wave Unisex Snapback Hat - White
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    Hari Mari

    Hari Mari Unisex Snapback Hat

    Elevate your casual style with the Hari Mari Sun Wave Hat, available at Simpson Outfitters. This classic snapback cap features an embroidered Hari Mari sun wave logo on the front, adding a touch of coastal flair to your ensemble. Designed with...
    $22.00
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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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