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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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Southern Tide

Fintastic Swim Trunk

MSRP:

Was:

Now: $89.50
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Southern Tide

Backrush Heather Lounge Short - Heather Mango

MSRP:

Was:

Now: $69.50
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Southern Tide

Backrush Heather Lounge Short - Heather Mist Green

MSRP:

Was:

Now: $69.50
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Southern Tide

Rip Channel Roswell 6" Performance Short - Steel Grey

MSRP:

Was:

Now: $79.50
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Southern Tide

Rip Channel Roswell 6" Performance Short - Blue Ridge

MSRP:

Was:

Now: $79.50
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Southern Tide

T3 Gulf 8" Brrr Performance Shorts - Aqua Breeze

MSRP:

Was:

Now: $99.50
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Southern Tide

T3 Gulf 8" Brrr Performance Shorts - Porto Blue

MSRP:

Was:

Now: $99.50
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Southern Tide

T3 Gulf 8" Brrr Performance Shorts - Cashmere Blue

MSRP:

Was:

Now: $99.50
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Michael's

Sailing Away Swim Trunks - Royal

MSRP:

Was:

Now: $98.50
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Michael's

Stretch Twill Short

MSRP:

Was:

Now: $78.00
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Michael's

Gingham Swim Trunk

MSRP:

Was:

Now: $98.50
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Helly Hansen

Cadiz Swim Trunk

MSRP:

Was:

Now: $55.00
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Helly Hansen

HP 1/2 Zip Pullover

MSRP:

Was:

Now: $70.00
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Helly Hansen

HP Racing Lifaloft Midlayer Jacket

MSRP:

Was:

Now: $200.00
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Helly Hansen

Salt Inshore Sailing Jacket

MSRP:

Was:

Now: $220.00
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Helly Hansen

Salt Navigator Sailing Jacket

MSRP:

Was:

Now: $260.00
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Helly Hansen

HP Foil Match Jacket

MSRP:

Was:

Now: $280.00
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Southern Tide

Santiago Stripe Intercoastal Short Sleeve Button Down Shirt

MSRP:

Was:

Now: $115.00
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Southern Tide

Coastal Tapestry Printed Intercoastal Short Sleeve Button Down Shirt

MSRP:

Was:

Now: $115.00
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Southern Tide

Sunrise Printed Intercoastal Short Sleeve Button Down Shirt

MSRP:

Was:

Now: $115.00

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From Chatham to Newport and Beyond

We feature styles that aren’t just perfect for your next vacation, but timeless men’s resort wear and essentials to last you all year long. Discover performance polos, plaid wovens, seersucker shorts and much more preppy-inspired, nautically-themed, men’s sportswear.

Your Destination for Your Favorite Brands

Outfit yourself for your next sun-seeking affair with new and comfortable looks from brands like:

Browse Island Pursuit’s selection of men’s resort-inspired sportswear. You can even filter our collection by brands, garment type, color, or size to find exactly what you need. And, don’t forget to share your Island Pursuit wear on Instagram – tag us with #islandpursuit!