Popular Preppy Clothing for Women & Men

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    Striped Contrast Trim Quarter Snap T-Shirt
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    $ 59.00
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    $ 59.00
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    Floral Tie Neck Lantern Sleeve Blouse
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    $ 49.00
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    $ 49.00
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    Kimmy Sun Farer Striped Crew Pullover by Southern Tide
    Regular Price
    $ 68.00
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    $ 68.00
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    Sleeveless Top in Royal Stewart Tartan Plaid by Castaway Clothing
    Regular Price
    $ 61.95
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    $ 61.95
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    $ 118.00
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    Ladies Button Down Flannel Shirt by Castaway Clothing
    Regular Price
    $ 61.95
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    $ 61.95
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    $ 118.00
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    Ladies Gingham Button Down Shirt with Embroidered Christmas Trees by Castaway Clothing
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    $ 135.00
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    $ 135.00
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    Royal Stewart Tunic Top with Velvet Trim by Castaway Clothing
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    $ 158.00
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    $ 158.00
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    Lively Leopard Print Faux Fur Poncho by Caroline Hill
    Regular Price
    $ 54.00
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    $ 54.00
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    Tatum Tunic in Shadow by Lauren James
    Regular Price
    $ 68.00
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    $ 68.00
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    Taylor Tunic Popover in Birmingham by The Southern Shirt Co.
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    $ 68.00
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    $ 68.00
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    Plaid Button Front Curved Hem Collared Shirt
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    $ 49.00
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    $ 49.00
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    Ranya Performance Quarter Zip Pullover by Southern Tide
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    $ 110.00
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    $ 110.00
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    Chilmark Relaxed Oxford Button Down by Vineyard Vines
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    $ 78.00
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    $ 78.00
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    Ladies Oxford Button Down Shirt with Royal Stewart Trim by Castaway Clothing
    Regular Price
    $ 118.00
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    $ 118.00
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    Carter Boyfriend Tunic in Blush by Lauren James
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    $ 72.00
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    $ 72.00
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    Seersucker Chilmark Relaxed Button Down by Vineyard Vines
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    $ 45.95
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    $ 45.95
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    $ 88.00
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    Taylor Tunic Popover in Nashville by The Southern Shirt Co.
    Regular Price
    $ 68.00
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    $ 68.00
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    Soft Sierra Raw Seam Mock by Dylan (True Grit)
    Regular Price
    $ 80.00
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    $ 80.00
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    The Wall Streeter Priss Blouse by Gretchen Scott Designs
    Regular Price
    $ 56.95
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    $ 56.95
    Regular Price
    $ 109.00
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    Sydney Snake Print Kimono by Caroline Hill
    Regular Price
    $ 44.00
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    $ 44.00
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    Paiton Multi-Striped Hoodie by Southern Tide
    Regular Price
    $ 108.00
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    $ 108.00
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    Lyndi Leopard Cozy Flannel Kimono by Caroline Hill
    Regular Price
    $ 44.00
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    $ 44.00
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    Tatum Tunic by Lauren James
    Regular Price
    $ 48.00
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    $ 48.00
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    Jersey Ruffneck 3/4 Sleeve Top by Gretchen Scott Designs
    Regular Price
    $ 99.00
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    $ 99.00
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    Hayden Boyfriend Flannel in Blush by Lauren James
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    $ 59.00
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    $ 59.00
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    Leopard Print Faux Fur Poncho by Caroline Hill
    Regular Price
    $ 40.00
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    $ 40.00
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    Pacific Plaid Chilmark Relaxed Button Down by Vineyard Vines
    Regular Price
    $ 78.00
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    $ 78.00
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    Hazelwood Tweed Poncho by Dubarry of Ireland
    Regular Price
    $ 299.00
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    $ 299.00
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    Margo Silk Tie Top by Lauren James
    Regular Price
    $ 78.00
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    $ 78.00
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    Leslie Wintertime Plaid Top by Southern Tide
    Regular Price
    $ 138.00
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    $ 138.00
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    Darbia Cashmere Feel Animal Print Kimono by Caroline Hill
    Regular Price
    $ 54.00
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    $ 54.00
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    Rumi Mixed Print Kimono by Caroline Hill
    Regular Price
    $ 24.00
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    $ 24.00
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    Ella Heather Turtle Neck Pullover by Southern Tide
    Regular Price
    $ 118.00
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    $ 118.00
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    Hayden Boyfriend Flannel in Navy by Lauren James
    Regular Price
    $ 59.00
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    $ 59.00
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    Carter Boyfriend Tunic in Shadow by Lauren James
    Regular Price
    $ 72.00
    Sale Price
    $ 72.00
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    Leopard Print Kimono by Caroline Hill
    Regular Price
    $ 26.00
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    $ 26.00
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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!