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Explore Men’s Preppy, Island-Inspired Resort Wear

Whether you’re lounging on a beach, surfing, hitting the links, or sailing, we feature men’s sports wear that captures classic American style with modern twists, all from brands you know and love.

From the best in performance shirts, button-down wovens to hybrid swim trunks, you’ll find everything you need at Island Pursuit.

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  • Chubbies The Moon Shadows Classic Swim Trunk 7"

    Chubbies

    The Moon Shadows Classic Swim Trunk 7"

    $69.50
  • Chubbies The Night Faunas Classic Swim Trunk 7"

    Chubbies

    The Night Faunas Classic Swim Trunk 7"

    $69.50
  • Chubbies The King Street Short Sleeve Button Up Shirt

    Chubbies

    The King Street Short Sleeve Button Up Shirt

    $64.50
  • Chubbies The Pinky Winky Short Sleeve Button Up Shirt

    Chubbies

    The Pinky Winky Short Sleeve Button Up Shirt

    $64.50
  • Chubbies The Neon Dream T-Shirt

    Chubbies

    The Neon Dream T-Shirt

    $29.50
  • Chubbies The Ocean Trifectas Classic Swim Trunk 7"

    Chubbies

    The Ocean Trifectas Classic Swim Trunk 7"

    $69.50
  • Chubbies The Desert Dawns Classic Swim Trunk 5.5"

    Chubbies

    The Desert Dawns Classic Swim Trunk 5.5"

    $69.50
  • Chubbies The World's Grayest Performance Short 8"

    Chubbies

    The World's Grayest Performance Short 8"

    $64.50
  • Chubbies The New Englands Performance Short 6"

    Chubbies

    The New Englands Performance Short 6"

    $64.50
  • Helly Hansen LIFA® Active Solen Graphic Hoodie

    Helly Hansen

    LIFA® Active Solen Graphic Hoodie

    $85.00
  • Helly Hansen Men's Crew Sailing Vest 2.0

    Helly Hansen

    Crew Sailing Vest 2.0

    $135.00
  • Helly Hansen Men’s Inshore Cup Sailing Jacket

    Helly Hansen

    Inshore Cup Sailing Jacket

    $250.00
  • Southern Tide Driver Carova Stripe Polo Shirt  Island Pursuit

    Southern Tide

    Driver Carova Stripe Polo Shirt - Coronet Blue

    $98.00
  • Southern Tide Sun Washed Seerscuker Camp Short Sleeve Sport Shirt | Island Pursuit | Free shipping over $100

    Southern Tide

    Sun Washed Seerscuker Camp Short Sleeve Sport Shirt - Paprika Red

    $118.00
  • Southern Tide Sun Washed Seerscuker Camp Short Sleeve Sport Shirt | Island Pursuit | Free shipping over $100

    Southern Tide

    Sun Washed Seerscuker Camp Short Sleeve Sport Shirt

    $118.00
  • Southern Tide Driver Paradise Palms Polo Shirt  Island Pursuit

    Southern Tide

    Driver Paradise Palms Polo Shirt - Classic White

    $98.00
  • Southern Tide Driver Dive In Polo Shirt | Island Pursuit

    Southern Tide

    Driver Dive In Polo Shirt - Teaberry Pink

    $98.00
  • Southern Tide That Floral Feeling Swim Trunk | Island Pursuit

    Southern Tide

    That Floral Feeling Swim Trunk - Apricot Blush Coral

    $98.00
  • Southern Tide Caps Off Swim Trunk | Island Pursuit

    Southern Tide

    Caps Off Swim Trunk - Subdued Blue

    $98.00