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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 Men's The Half Elastic 7" Surf Shorts - Bungalow

    Johnnie-O

    The Half Elastic 7" Surf Shorts - Bungalow

    $89.00
  • Johnnie-O Men's The Half Elastic 7" Surf Shorts - Big Blue

    Johnnie-O

    The Half Elastic 7" Surf Shorts - Big Blue

    $89.00
  • Johnnie-O Men's Travis Performance Button Down Shirt

    Johnnie-O

    Travis Performance Button Down Shirt

    $138.00
  • Johnnie-O Men's Hoppin Performance Drawstring Hoodie

    Johnnie-O

    Hoppin Performance Drawstring Hoodie

    $168.00
  • Johnnie-O Men's The Course Performance T-Shirt

    Johnnie-O

    The Course Performance T-Shirt

    $78.00
  • Johnnie-O Men's Bronte Performance Jersey Polo

    Johnnie-O

    Bronte Performance Jersey Polo

    $98.00
  • Johnnie-O Mens Top O' The Morning Featherweight Performance Polo

    Johnnie-O

    Top O' The Morning Featherweight Performance Polo

    $110.00
  • Johnnie-O Men's Glidey Featherweight Performance Polo

    Johnnie-O

    Glidey Featherweight Performance Polo

    $110.00
  • Johnnie-O Men's Springwood Performance Jersey Polo

    Johnnie-O

    Springwood Performance Jersey Polo

    $98.00
  • Johnnie-O Men's Stetsons Performance Mesh Polo

    Johnnie-O

    Performance Mesh Polo - Stetson Stripe

    $110.00
  • Helly Hansen Men's Crew Midlayer Jacket 2.0

    Helly Hansen

    M Crew Midlayer Jacket 2.0

    $185.00
  • Helly Hansen Men's HP Fleece Jacket 2.0

    Helly Hansen

    M HP Fleece Jacket 2.0

    $130.00
  • Johnnie-O Men's Newport 5-Pocket Cotton Pant 32"

    Johnnie-O

    Newport 5-Pocket Cotton Pants 32"

    $148.00
  • Johnnie-O Men's Newport 5-Pocket Cotton Pant 30"

    Johnnie-O

    Newport 5-Pocket Cotton Pants 30"

    $148.00
  • Helly Hansen Men's Crew Sailing Vest 2.0

    Helly Hansen

    Crew Sailing Vest 2.0

    $135.00
  • Helly Hansen Men’s Crew Hooded Sailing Jacket 2.0

    Helly Hansen

    M Crew Hooded Jacket 2.0

    $175.00
  • Johnnie-O Men's Hanks "Lightweight Sully" 1/4 Zip Pullover

    Johnnie-O

    Hanks "Lightweight Sully" 1/4 Zip Pullover

    $148.00
  • Johnnie-O Men's Mulligan 9" Performance Woven Shorts

    Johnnie-O

    Mulligan Performance Woven Shorts

    $98.00
  • Johnnie-OMen's Nassau 8" Cotton Blend Shorts

    Johnnie-O

    Nassau 8" Cotton Blend Shorts

    $98.00
  • Johnnie-O Men's Brennan 2.0 Long Sleeve Pocket T-Shirt

    Johnnie-O

    Brennan 2.0 Long Sleeve Pocket T-Shirt

    $58.00