MEN

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.

Sort by
  • Vanilla Latte Crew Sweatshirt

    Chubbies

    Vanilla Latte Crew Sweatshirt

    $59.50
  • The Vanilla Lattes 5.5" (Soft Terry Short)

    Chubbies

    The Vanilla Lattes 5.5" (Soft Terry Short)

    $44.50
  • Surfside Short Sleeve Sportshirt

    Chubbies

    Surfside Short Sleeve Sportshirt

    $64.50
  •  Brunchin Blossom Short Sleeve Sportshirt

    Chubbies

    Brunchin Blossom Short Sleeve Sportshirt

    $64.50
  • The Resort Wear Short Sleeve Sportshirt

    Chubbies

    The Resort Wear Short Sleeve Sportshirt

    $64.50
  • The Gravel Roads 5.5" (Classic Swim Trunk)

    Chubbies

    The Gravel Roads 5.5" (Classic Swim Trunk)

    $69.50
  • The Floral Reefs 6" (Boardshort)

    Chubbies

    The Floral Reefs 6" (Boardshort)

    $69.50
  • The Havana Nights 5.5" (Lined Classic Swim Trunk)

    Chubbies

    The Havana Nights 5.5" (Lined Classic Swim Trunk)

    $69.50
  • The Cruise It or Lose Its 5.5" (Classic Swim Trunk)

    Chubbies

    The Cruise It or Lose Its 5.5" (Classic Swim Trunk)

    $69.50
  • The Khakinators 6" (Everywear Stretch)

    Chubbies

    The Khakinators 6" (Everywear Stretch)

    $64.50
  • The Tropical Flight Short Sleeve T-Shirt

    Chubbies

    The Tropical Flight Short Sleeve T-Shirt

    $29.50
  • The PRs 5.5" (Compression Lined)

    Chubbies

    The PRs 5.5" (Compression Lined)

    $69.50
  • The Good Boys 7" (Compression Lined)

    Chubbies

    The Good Boys 7" (Compression Lined)

    $69.50
  • The Retro Sets 5.5" (Classic Swim Trunk)

    Chubbies

    The Retro Sets 5.5" (Classic Swim Trunk)

    $69.50
  • The Main Sail Short Sleeve T-Shirt

    Chubbies

    The Main Sail Short Sleeve T-Shirt

    $29.50
  • The Back to the Futures 7" (Lined Classic Swim Trunk)

    Chubbies

    The Back to the Futures 7" (Lined Classic Swim Trunk)

    $79.50
  • The Favs 7" (Classic Swim Trunk)

    Chubbies

    The Favs 7" (Classic Swim Trunk)

    $69.50
  • The Favs 5.5" (Classic Swim Trunk)

    Chubbies

    The Favs 5.5" (Classic Swim Trunk)

    $69.50
  • The Prism Parties 5.5" (Schwort)

    Chubbies

    The Prism Parties 5.5" (Schwort)

    $69.50
  • The Cherry Blossoms 6" (Everywear Stretch)

    Chubbies

    The Cherry Blossoms 6" (Everywear Stretch)

    $64.50