Popular Preppy Clothing for Women & Men

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    Alder Longshore Shirt by Vineyard Vines - Country Club Prep
    Alder Longshore Shirt by Vineyard Vines
    $ 51.95
    $ 51.95
    $ 98.50
    Save 48%
    Relaxed Hoodie Shep Shirt by Vineyard Vines - Country Club Prep
    Relaxed Hoodie Shep Shirt by Vineyard Vines
    $ 50.95
    $ 50.95
    $ 98.00
    SOLD OUT
    Harpers Longshore Shirt by Vineyard Vines - Country Club Prep
    Harpers Longshore Shirt by Vineyard Vines
    $ 51.95
    $ 51.95
    $ 98.50
    SOLD OUT
    Mountain Sweater Fleece 1/2 Zip Pullover by Vineyard Vines - Country Club Prep
    Mountain Sweater Fleece 1/2 Zip Pullover by Vineyard Vines
    $ 125.00
    $ 125.00
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    Classic Whale Embroidered Oxford Shep Shirt by Vineyard Vines - Country Club Prep
    Classic Whale Embroidered Oxford Shep Shirt by Vineyard Vines
    $ 98.00
    $ 98.00
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    Collegiate Shep Shirt in Gray Heather by Vineyard Vines - Country Club Prep
    Collegiate Shep Shirt in Gray Heather by Vineyard Vines
    $ 98.50
    $ 98.50
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    Heritage Sherpa 1/2-Zip in Moonshine by Vineyard Vines - Country Club Prep
    Heritage Sherpa 1/2-Zip in Moonshine by Vineyard Vines
    $ 148.00
    $ 148.00
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    Chilmark Relaxed Oxford Button Down by Vineyard Vines - Country Club Prep
    Chilmark Relaxed Oxford Button Down by Vineyard Vines
    $ 78.00
    $ 78.00
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    Collegiate Shep Shirt in Vineyard Navy by Vineyard Vines - Country Club Prep
    Collegiate Shep Shirt in Vineyard Navy by Vineyard Vines
    $ 51.95
    $ 51.95
    $ 98.50
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    Darvo Performance Murray Shirt by Vineyard Vines - Country Club Prep
    Darvo Performance Murray Shirt by Vineyard Vines
    $ 115.00
    $ 115.00
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    Garment Dyed Oxford Slim Stretch Tucker Shirt in Ocean Breeze by Vineyard Vines - Country Club Prep
    Garment Dyed Oxford Slim Stretch Tucker Shirt in Ocean Breeze by Vineyard Vines
    $ 98.50
    $ 98.50
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    Sweater Fleece Shep Shirt Vest in Pebble by Vineyard Vines - Country Club Prep
    Sweater Fleece Shep Shirt Vest in Pebble by Vineyard Vines
    $ 115.00
    $ 115.00
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    Performance Mesh Back Shep Shirt in Deep Bay by Vineyard Vines - Country Club Prep
    Performance Mesh Back Shep Shirt in Deep Bay by Vineyard Vines
    $ 125.00
    $ 125.00
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    Belle Haven Plaid Slim Tucker Shirt in Sailors Red by Vineyard Vines - Country Club Prep
    Belle Haven Plaid Slim Tucker Shirt in Sailors Red by Vineyard Vines
    $ 98.50
    $ 98.50
    Party in the USA Pocket T-Shirt by Vineyard Vines - Country Club Prep
    Party in the USA Pocket T-Shirt by Vineyard Vines
    $ 42.00
    $ 42.00
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    Stretch Breaker Pants in Lobster Reef by Vineyard Vines - Country Club Prep
    Stretch Breaker Pants in Lobster Reef by Vineyard Vines
    $ 51.95
    $ 51.95
    $ 98.50
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    Long Sleeve Overdyed Heathered T-Shirt in Gray Heather by Vineyard Vines - Country Club Prep
    Long Sleeve Overdyed Heathered T-Shirt in Gray Heather by Vineyard Vines
    $ 48.00
    $ 48.00
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    Mill Hill Flannel Classic Crosby Shirt in Moonshine by Vineyard Vines - Country Club Prep
    Mill Hill Flannel Classic Crosby Shirt in Moonshine by Vineyard Vines
    $ 98.50
    $ 98.50
    SOLD OUT
    Seersucker Chilmark Relaxed Button Down by Vineyard Vines - Country Club Prep
    Seersucker Chilmark Relaxed Button Down by Vineyard Vines
    $ 45.95
    $ 45.95
    $ 88.00
    SOLD OUT
    On-The-Go Pants by Vineyard Vines - Country Club Prep
    On-The-Go Pants by Vineyard Vines
    $ 65.95
    $ 65.95
    $ 125.00
    SOLD OUT
    Sherpa Harbor 1/2 Zip Pullover by Vineyard Vines - Country Club Prep
    Sherpa Harbor 1/2 Zip Pullover by Vineyard Vines
    $ 148.00
    $ 148.00
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    Long Sleeve Slub Whale Hoodie by Vineyard Vines - Country Club Prep
    Long Sleeve Slub Whale Hoodie by Vineyard Vines
    $ 98.00
    $ 98.00
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    Custom Vintage Whale Graphic Long Sleeve Tee Shirt in Royal Blue by Vineyard Vines - Country Club Prep
    Custom Vintage Whale Graphic Long Sleeve Tee Shirt in Royal Blue by Vineyard Vines
    $ 48.00
    $ 48.00
    SOLD OUT
    Carleton Gingham Classic Stretch Tucker Shirt in Moonshine by Vineyard Vines - Country Club Prep
    Carleton Gingham Classic Stretch Tucker Shirt in Moonshine by Vineyard Vines
    $ 98.50
    $ 98.50
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    Longshore Kelby Flannel Shirt by Vineyard Vines - Country Club Prep
    Longshore Kelby Flannel Shirt by Vineyard Vines
    $ 98.50
    $ 98.50
    SOLD OUT
    Stoney Hill Classic Burgee Shirt Shirt in Starboard Green by Vineyard Vines - Country Club Prep
    Stoney Hill Classic Burgee Shirt Shirt in Starboard Green by Vineyard Vines
    $ 98.50
    $ 98.50
    SOLD OUT
    Stillwater Chest Pocket Sherpa 1/2 Zip Pullover by Vineyard Vines - Country Club Prep
    Stillwater Chest Pocket Sherpa 1/2 Zip Pullover by Vineyard Vines
    $ 148.00
    $ 148.00
    SOLD OUT
    Custom USA Flag Pocket T-Shirt in Blue Blazer by Vineyard Vines - Country Club Prep
    Custom USA Flag Pocket T-Shirt in Blue Blazer by Vineyard Vines
    $ 21.95
    $ 21.95
    $ 42.00
    SOLD OUT
    Saltwater 1/2 Zip Pullover by Vineyard Vines - Country Club Prep
    Saltwater 1/2 Zip Pullover by Vineyard Vines
    $ 98.50
    $ 98.50
    SOLD OUT
    Bora Performance Murray Shirt by Vineyard Vines - Country Club Prep
    Bora Performance Murray Shirt by Vineyard Vines
    $ 115.00
    $ 115.00
    SOLD OUT
    The Island Shot Pocket T-Shirt by Vineyard Vines - Country Club Prep
    The Island Shot Pocket T-Shirt by Vineyard Vines
    $ 42.00
    $ 42.00
    SOLD OUT
    Performance Mesh Back Shep Shirt in Medium Heather Grey by Vineyard Vines - Country Club Prep
    Performance Mesh Back Shep Shirt in Medium Heather Grey by Vineyard Vines
    $ 125.00
    $ 125.00
    SOLD OUT
    Heritage Sherpa 1/2-Zip in Camel by Vineyard Vines - Country Club Prep
    Heritage Sherpa 1/2-Zip in Camel by Vineyard Vines
    $ 148.00
    $ 148.00
    SOLD OUT
    Boldwater Plaid Performance Tucker Shirt in Sailors Red by Vineyard Vines - Country Club Prep
    Boldwater Plaid Performance Tucker Shirt in Sailors Red by Vineyard Vines
    $ 115.00
    $ 115.00
    SOLD OUT
    Tri-Color Vintage Whale Long Sleeve Pocket Tee by Vineyard Vines - Country Club Prep
    Tri-Color Vintage Whale Long Sleeve Pocket Tee by Vineyard Vines
    $ 48.00
    $ 48.00
    SOLD OUT
    Long Sleeve Striped Whale Terry Hoodie by Vineyard Vines - Country Club Prep
    Long Sleeve Striped Whale Terry Hoodie by Vineyard Vines
    $ 50.95
    $ 50.95
    $ 98.00

    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!