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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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  • Johnnie-O Jerome Flannel Shacket

    Johnnie-O

    Jerome Flannel Shacket

    $138.00
  • Johnnie-O Coggins Stretch Flannel Lodge Shirt

    Johnnie-O

    Coggins Shirt Jacket

    $228.00
  • Johnnie-O Bender Melange Hoodie Pullover

    Johnnie-O

    Bender Melange Hoodie Pullover

    $128.00
  • Johnnie-O Altos Performance Jogger

    Johnnie-O

    Altos Performance Jogger

    $128.00
  • Johnnie-O Avry Camo Full Zip Hoodie

    Johnnie-O

    Avry Camo Full Zip Hoodie

    $118.00
  • Johnnie-O Acadia PREP-FORMANCE Button Up Shirt

    Johnnie-O

    Acadia PREP-FORMANCE Button Up Shirt

    $138.00
  • Johnnie-O Mead Performance Button Up Shirt

    Johnnie-O

    Mead Performance Button Up Shirt

    $138.00
  • Johnnie-O Sasser Performance 1/4 Zip Pullover

    Johnnie-O

    Sasser Performance 1/4 Zip Pullover

    $118.00
  • Johnnie-O Talon Performance T-Shirt Hoodie

    Johnnie-O

    Talon Performance T-Shirt Hoodie

    $118.00
  • Michaels Portifino Long Sleeve Linen Shirt in a multi pattern with a teal background

    Michael's

    Portifino Long Sleeve Linen Shirt

    $148.00
  • Michaels Corvettes Pima Cotton Polo featuring Multi colored Corvettes on a Blue Background

    Michael's

    Corvettes Pima Cotton Stretch Full Button Polo

    $118.00
  • Michael's Swimwear Classic 8" Men's shorts in Nantucket Red

    Michael's

    Classic 8" Men's shorts

    $98.00
  • Michael's Swimwear Turtles White Swim Trunk

    Michael's

    Turtles White Swim Trunk

    $98.00
  • Back view of Michael's Swimwear Coral Jungle Swim Trunk

    Michael's

    Coral Jungle Swim Trunk

    $98.00
  • Michael's Swimwear Multi-colored Funky Pineapple Swim Trunk

    Michael's

    Funky Pineapple Swim Trunk

    $98.00
  • Michael's Swimwear Fish Swim Trunk

    Michael's

    Fish Swim Trunk

    $98.00
  • Michael's Swimwear Beach Umbrellas Swim Trunks

    Michael's

    Beach Umbrellas Swim Trunks

    $98.00
  • Back view of the Michael's Swimwear Flip Flop print swim trunks

    Michael's

    Flip Flop Swim Trunks

    $98.00
  • Michael's Swimwear Turtles Navy Swim Trunk

    Michael's

    Turtles Navy Swim Trunk

    $98.00
  • Michaels Crew Short Sleeve Tee in Coral Heather

    Michael's

    Crew Short Sleeve Tee

    $49.50