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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 Maarten Everyday Performance Button Down Shirt Johnnie-O Men's Maarten Everyday Performance Button Down Shirt

    Maarten Everyday Performance Button Down Shirt

    Johnnie-O
    $138.00
    Everyday Performance button-downs 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 Kamper Performance Flannel Button Down Shirt Johnnie-O Men's Kamper Performance Flannel Button Down Shirt

    Kamper Performance Flannel Button Down Shirt

    Johnnie-O
    $158.00
    The best flannel out there—this premium ultra-soft cotton-based flannel keeps your warm without the itchiness and makes chopping wood (or just tossing around the football) that much easier thanks to a touch of stretch. Long sleeve Button down...
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    $158.00
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  • Johnnie-O Men's Olie Featherweight Performance Button Down Shirt Johnnie-O Men's Olie Featherweight Performance Button Down Shirt

    Olie Featherweight Performance Button Down Shirt

    Johnnie-O
    $138.00
    Featherweight Performance button-downs are the lightest performance sport shirts we make. Made with a lightweight blend of nylon, lyocell and stretch that is naturally cool to the touch—this is how you keep things light and comfortable all day long...
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  • Johnnie-O Men's Hendley Everyday Performance Button Down Shirt Johnnie-O Men's Hendley Everyday Performance Button Down Shirt

    Hendley 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 Morganstern Natural Performance Button Down Shirt Johnnie-O Men's Morganstern Natural Performance Button Down Shirt

    Morganstern 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 Weyburn Lakewave Baseball Sweatshirt Johnnie-O Men's Weyburn Lakewave Baseball Sweatshirt

    Weyburn Lakewave Baseball Sweatshirt

    Johnnie-O
    $128.00
    Named for its distinctive baseball style, this sweatshirt is made with our Lakewave fabric, named for it's noticeable texture that resembles—you guessed it—waves on a lake. It's finished with classic contrast sleeves and the "whistlestop"...
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  • Johnnie-O Men's Penns Performance Hoodie Pullover Johnnie-O Men's Penns Performance Hoodie Pullover

    Penns Performance Hoodie Pullover

    Johnnie-O
    $138.00
    A high performance t-shirt hoodie that feels as good as it looks. The Penns is made of a performance fabric blend that moves with you when you're on the go. Whether you're going out for a timed run or a coffee run, you'll look good and feel great doing...
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  • Johnnie-O Men's Freeborne Performance 1/4 Zip Pullover Johnnie-O Men's Freeborne Performance 1/4 Zip Pullover

    Freeborne Performance 1/4 Zip Pullover

    Johnnie-O
    $118.00
    We took our favorite lightweight performance fabric and upgraded it with a peached finish to make the softest base layer you'll own. And not for nothing, it's made with UPF 50 for sun protection. Lightweight base layer 1/4 zip Ultra soft peached...
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    $118.00
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  • Helly Hansen Men's Men's Crew Hooded Pile Jacket Helly Hansen Men's Men's Crew Hooded Pile Jacket

    Men's Crew Hooded Pile Jacket

    Helly Hansen
    $205.00
    Based on our heritage pile styles, the Men's Crew Hooded Pile Jacket combines warmth and waterproof protection for sailors, ashore or aboard. Our HELLY TECH® Protection technology and full seam sealing keep you dry and comfortable while a pile fleece...
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    $205.00
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  • Helly Hansen Men's Men's Chill Jacket 3.0 Helly Hansen Men's Men's Chill Jacket 3.0

    Men's Chill Jacket 3.0

    Helly Hansen
    $315.00
    The Men's Chill Jacket 3.0 is an updated take on our renowned fall-winter staple. Engineered with waterproof/breathable HELLY TECH® Protection technology and with sealed seams, this jacket ensures both waterproofness and breathability. The...
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    $315.00
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  • Helly Hansen Men's Gravity Insulated Ski Jacket Helly Hansen Men's Gravity Insulated Ski Jacket

    Men's Gravity Insulated Ski Jacket

    Helly Hansen
    $305.00
    The perfect jacket for a perfect ski day blends our trusted technology with clean, mountain-inspired style. The HELLY TECH® Performance 2-layer technology is waterproof/breathable and windproof. PrimaLoft® BLACK delivers lightweight warmth. The...
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  • Kuhl Men's Aktivator Fleece Performance Full Zip Jacket Kuhl Men's Aktivator Fleece Performance Full Zip Jacket

    Aktivator Fleece Performance Full Zip Jacket

    Kuhl
    $169.00
    What Makes It KÜHL? The temperature-regulating AKTIVATOR® Full Zip defies and disrupts the iconic fleece jacket. Our body-mapped design features two weights of premium fleece to place heavyweight heat where you want it, and lighter-weight...
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