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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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  • Saint James Sherbrooke High Buttoned Collar Pullover Sweater

    Saint James

    Sherbrooke 1/4 Zip Pullover Sweater

    $299.00
  • Prana Ashland Corduroy Jacket

    Prana

    Ashland Corduroy Jacket

    $180.00
  • Prana Westbrook Flannel Shirt

    Prana

    Westbrook Flannel Shirt

    $99.00
  • Front view on the Southern Tide Solid Swim Trunk 2.0 in True Navy

    Southern Tide

    Solid Swim Trunk 2.0 - True Navy

    $89.50
  • Southern Tide Solid Swim Trunk 2.0 in Sunkist Coral

    Southern Tide

    Solid Swim Trunk 2.0 - Sunkist Coral

    $89.50
  • Southern Tide Solid Swim Trunk 2.0 in Ocean Channel

    Southern Tide

    Solid Swim Trunk 2.0 - Ocean Channel

    $89.50
  • Southern Tide Solid Swim Trunk 2.0 in Tidal Wave Blue

    Southern Tide

    Solid Swim Trunk 2.0 - Tidal Wave

    $89.50
  • HIHO Caribbean UPF 50 Eli Tech Hoodie | Island Pursuit | Free shipping over $100

    Hi Ho

    UPF 50 Eli Tech Hoodie

    $84.00
  • HIHO Caribbean's Jeremy Linen Sportshirt | Island Pursuit | Free shipping over $100

    Hi Ho

    Jeremy Linen Sportshirt

    $125.00
  • Avid Cabo Performance Fishing Shirt 50+ UPF

    Avid Sportswear

    Cabo Performance Fishing Shirt 50+ UPF

    $74.00
  • On Sale!
    Back view of AVID Sportswear Promise Land Short Sleeve T-Shirt in Seafoam

    Avid Sportswear

    Promise Land Short Sleeve T-Shirt

    Was: $30.00
    Now: $15.00
  • On Sale!
    Avid Merica T-Shirt in White features the Avid hook logo in Teal on back

    Avid Sportswear

    Merica T-Shirt

    Was: $30.00
    Now: $15.00
  • Chubbies Magic Apex Swimmer 7" Trunk in Teal Shark | Island Pursuit | Free shipping over $100

    Chubbies

    Magic Apex Swimmer 7" Trunk

    $74.50
  • Chubbies Beaches 5.5" Swim Trunk | Island Pursuit | Free shipping over $100

    Chubbies

    Beaches 5.5" Swim Trunk

    $69.50
  • Chubbies Rum Punches 7" Swimtrunk in Bright Blue | Island Pursuit | Free shipping over $100

    Chubbies

    Rum Punches 7" Swimtrunk

    $69.50
  • Chubbies Raptor Trainer 5.5" Swim Trunk in Coral | Island Pursuit | Free shipping over $100

    Chubbies

    Raptor Trainer 5.5" Swim Trunk

    $74.50
  • Chubbies Roaring Time 5.5" Swim Trunk | Island Pursuit | Free shipping over $100

    Chubbies

    Roaring Time 5.5" Swim Trunk

    $74.50
  • Chubbies Neon Lake 5"5 Swim Trunk | Island Pursuit | Free shipping ove $100

    Chubbies

    Neon Lake 5"5 Swim Trunk

    $69.50
  • Chubbies The Floral Reefs 6" Boardshort in Dark Blue with a Floral Pattern in Coral, yellow and teal

    Chubbies

    The Floral Reefs 6" (Boardshort)

    $69.50
  • Chubbies The Retro Sets 7" Stretch Swim Trunk

    Chubbies

    The Retro Sets 7" Stretch Swim Trunk

    $69.50
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