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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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  • Helly Hansen Men's HH Tech Crew Long Sleeve 2.0 Helly Hansen Men's HH Tech Crew Long Sleeve 2.0

    M HH Tech Crew Long Sleeve 2.0

    Helly Hansen
    $35.00 - $40.00
    Lightweight performance, built for the sun ☀️ The Helly Hansen Men’s HH Tech Crew Long Sleeve 2.0 is designed to keep you cool, dry, and protected during any outdoor activity. Whether you're sailing, hiking, or spending long days in...
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  • Helly Hansen Men's HH Tech Hoodie Helly Hansen Men's HH Tech Hoodie

    HH Tech Hoodie

    Helly Hansen
    $40.00 - $45.00
    Lightweight protection, built for the sun ☀️?‍♂️ The Helly Hansen Men’s HH Tech Hoodie is your go-to layer for active days outdoors. Whether you're hiking, trail running, or sailing, this performance hoodie keeps you cool, dry, and...
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  • Helly Hansen Men's HP Racing Hooded Jacket 2.0 Helly Hansen Men's HP Racing Hooded Jacket 2.0

    M HP Racing Hooded Jacket 2.0

    Helly Hansen
    $200.00 - $210.00
    Built for competitive sailors, the Men's HP Racing Hooded Jacket 2.0 provides waterproof protection and flexibility, with a range of features to enhance your performance in inshore conditions. This updated sporty style is inspired by the aerodynamic...
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  • Johnnie-O Men's Westwood Performance Button Down Shirt Johnnie-O Men's Westwood Performance Button Down Shirt

    Westwood Performance Button Down Shirt

    Johnnie-O
    $138.00
    Everyday Performance button-ups are designed to infuse athletic benefits into your go-to shirts. With a wrinkle-resistant nylon, Coolmax® and bamboo blend that wicks moisture, breathes well and stretches, this shirt ensures you'll always look and...
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    $138.00
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  • Johnnie-O Men's Melrose Melrose Cotton Linen Shorts 7" Johnnie-O Men's Melrose Melrose Cotton Linen Shorts 7"

    Melrose Melrose Cotton Linen Shorts 7"

    Johnnie-O
    $118.00
    Designed like a classic Bermuda-style short with lightweight cotton/linen fabric, these shorts go the extra mile with a garment-dye process that gives them the perfect lived-in look. Garment dyed shorts Pic stitch detail on fly Slash pockets Double...
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    $118.00
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  • Johnnie-O Men's Masson Natural Performance Button Down Shirt Johnnie-O Men's Masson Natural Performance Button Down Shirt

    Masson Natural Performance Button Down Shirt

    Johnnie-O
    $138.00
    This button-down is made with a beautiful cotton and nylon performance blend that stretches and wicks moisture and features a hidden button-down collar. Finished with goosefoot and shanked buttons and our signature Tweener Button® which is hidden...
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  • Johnnie-O Men's The Half Elastic 7" Surf Shorts - Bungalow Johnnie-O Men's The Half Elastic 7" Surf Shorts - Bungalow

    The Half Elastic 7" Surf Shorts - Bungalow

    Johnnie-O
    $89.00
    These suits feature thoughtfully designed fun prints with pops of color throughout. We added netting to the interior for added comfort and brought the inseam up to 7". Made with a poly/cotton/spandex blend, these surf shorts are durable, soft, and...
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  • Johnnie-O Men's The Half Elastic 7" Surf Shorts - Big Blue Johnnie-O Men's The Half Elastic 7" Surf Shorts - Big Blue

    The Half Elastic 7" Surf Shorts - Big Blue

    Johnnie-O
    $89.00
    These suits feature thoughtfully designed fun prints with pops of color throughout. We added netting to the interior for added comfort and brought the inseam up to 7". Made with a poly/cotton/spandex blend, these surf shorts are durable, soft, and...
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  • Johnnie-O Men's Travis Performance Button Down Shirt Johnnie-O Men's Travis Performance Button Down Shirt

    Everyday Performance Button Down Shirt

    Johnnie-O
    $138.00
    Everyday Performance button-ups are designed to infuse athletic benefits into your go-to shirts. With a wrinkle-resistant nylon, Coolmax® and bamboo blend that wicks moisture, breathes well and stretches, this shirt ensures you'll always look and...
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  • Johnnie-O Men's The Course Performance T-Shirt Johnnie-O Men's The Course Performance T-Shirt

    The Course Performance T-Shirt

    Johnnie-O
    $78.00
    An ideal active performance top is soft to the touch, lightweight, sun-blocking and moisture wicking. Designed with hybrid style in mind, this tee offers the technical details you want for days on the course or hitting the gym, and it also looks classic...
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    $78.00
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  • Alashan cashmere Men's Cotton Cashmere Classic V-Neck Pullover Alashan cashmere Cotton Cashmere Classic V-Neck Pullover in Montauk Blue

    Men's Cotton Cashmere Classic V-Neck Pullover

    Alashan Cashmere
    $135.00
    Refine your look with our best-selling Classic V-Neck Pullover. This lightweight cotton cashmere blend allows for a stylish look with a breathable feel.  Soft blend of fine cotton and super fine Inner Mongolian cashmere (95/5) in 2ply yarn...
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    $135.00
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  • Alashan Cashmere Men's Cotton Cashmere Raglan Sweatshirt Alashan Cashmere Men's Cotton Cashmere Raglan Sweatshirt

    Men's Cotton Cashmere Raglan Sweatshirt

    Alashan Cashmere
    $128.00
    Add luxury to your casual style with the Raglan Sweatshirt. Crafted with attention to detail in our lightweight and soft cotton cashmere blend, this pullover is perfect for layering under a jacket or over a t-shirt. Elevate your casual style with this...
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