Popular Preppy Clothing for Women & Men

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    Stretch Breaker Pants in Anchor Gray by Vineyard Vines
    Regular Price
    $ 51.95
    Sale Price
    $ 51.95
    Regular Price
    $ 98.50
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    Oakfield Performance Vest by Vineyard Vines
    Regular Price
    $ 65.95
    Sale Price
    $ 65.95
    Regular Price
    $ 125.00
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    Edgartown Lightweight Shep Shirt by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Pacific Plaid Chilmark Relaxed Button Down by Vineyard Vines
    Regular Price
    $ 78.00
    Sale Price
    $ 78.00
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    Quilted Vest by Vineyard Vines
    Regular Price
    $ 168.00
    Sale Price
    $ 168.00
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    Full Zip Hoodie in Medium Heather Grey by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Placed Chest Stripe Rugby Shirt by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Bonfire Relaxed Funnel Neck Shep Shirt by Vineyard Vines
    Regular Price
    $ 118.00
    Sale Price
    $ 118.00
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    Buttonbush Check Slim Murray Shirt in Sailors Red by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Striped Sankaty 1/2-Zip Pullover by Vineyard Vines
    Regular Price
    $ 115.00
    Sale Price
    $ 115.00
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    Cades Tucker Shirt by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Morgan Way Plaid Classic Crosby Shirt in Ocean Breeze by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    St. Kitt's Sankaty Performance Polo by Vineyard Vines
    Regular Price
    $ 85.00
    Sale Price
    $ 85.00
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    Riverbank Plaid Slim Murray Shirt in Desert Green by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Full Zip Hoodie in Deep Bay by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Belle Haven Plaid Slim Tucker Shirt in Moonshine by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Shore Seersucker Classic Shep Shirt by Vineyard Vines
    Regular Price
    $ 98.00
    Sale Price
    $ 98.00
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    Heritage Sherpa Vest in Camel by Vineyard Vines
    Regular Price
    $ 128.00
    Sale Price
    $ 128.00
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    Tradewinds Flannel Slim Tucker Shirt in Sailors Red by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Heritage Sherpa Vest in Moonshine by Vineyard Vines
    Regular Price
    $ 66.95
    Sale Price
    $ 66.95
    Regular Price
    $ 128.00
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    Grier Stripe Mix Wrap Dress by Vineyard Vines
    Regular Price
    $ 148.00
    Sale Price
    $ 148.00
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    Carleton Gingham Classic Stretch Tucker Shirt in Spinnaker by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Camo Sherpa Harbor Vest by Vineyard Vines
    Regular Price
    $ 128.00
    Sale Price
    $ 128.00
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    Sherpa Harbor Vest by Vineyard Vines
    Regular Price
    $ 128.00
    Sale Price
    $ 128.00
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    Kettle Cove Classic Tucker Shirt in Barracuda by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Jeep Back C.C. Prep Long Sleeve Tee Shirt in White Cap by Vineyard Vines
    Regular Price
    $ 24.95
    Sale Price
    $ 24.95
    Regular Price
    $ 48.00
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    Long Sleeve Overdyed Heathered T-Shirt in Deep Bay by Vineyard Vines
    Regular Price
    $ 48.00
    Sale Price
    $ 48.00
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    Long Sleeve Overdyed Heathered T-Shirt in Capri Blue by Vineyard Vines
    Regular Price
    $ 48.00
    Sale Price
    $ 48.00
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    Alicetown Gingham Chilmark Classic Button Down by Vineyard Vines
    Regular Price
    $ 40.95
    Sale Price
    $ 40.95
    Regular Price
    $ 78.00
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    The Flats Cast Long Sleeve Pocket T-Shirt by Vineyard Vines
    Regular Price
    $ 48.00
    Sale Price
    $ 48.00
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    Stillwater Sherpa Vest by Vineyard Vines
    Regular Price
    $ 66.95
    Sale Price
    $ 66.95
    Regular Price
    $ 128.00
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    Fine Striped Margo Shirt Dress by Vineyard Vines
    Regular Price
    $ 138.00
    Sale Price
    $ 138.00
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    Boldwater Plaid Performance Slim Tucker Shirt in Starboard Green by Vineyard Vines
    Regular Price
    $ 115.00
    Sale Price
    $ 115.00
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    Long Sleeve Edgartown Vintage Whale Hoodie by Vineyard Vines
    Regular Price
    $ 55.00
    Sale Price
    $ 55.00
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    Woodhouse Garment Dyed Shep Shirt by Vineyard Vines
    Regular Price
    $ 125.00
    Sale Price
    $ 125.00
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    Carleton Gingham Classic Stretch Tucker Shirt in Hammerhead by Vineyard Vines
    Regular Price
    $ 98.50
    Sale Price
    $ 98.50
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    Everyone likes to stand out in a crowd, but there's wisdom in large numbers. These are the most popular preppy products on our site, and by extension, on the planet!