Popular Preppy Clothing for Women & Men

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    Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson
    Regular Price
    $ 295.00
    Sale Price
    $ 295.00
    Regular Price
    $ 295.00
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    Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson
    Regular Price
    $ 425.00
    Sale Price
    $ 425.00
    Regular Price
    $ 425.00
    Unit Price
    per 
    Dancing Bears Downing Bit Loafer by Smathers & Branson
    Regular Price
    $ 295.00
    Sale Price
    $ 295.00
    Regular Price
    $ 295.00
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    per 
    Save 39%
    Dapper Ribbon Bit Driving Shoes by Country Club Prep
    Regular Price
    $ 159.00
    Sale Price
    $ 159.00
    Regular Price
    $ 260.00
    Unit Price
    per 
    SOLD OUT
    Preston Deerskin Tassel Loafer by Country Club Prep
    Regular Price
    $ 320.00
    Sale Price
    $ 320.00
    Regular Price
    $ 320.00
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    Navy Camo Downing Bit Loafer by Smathers & Branson
    Regular Price
    $ 295.00
    Sale Price
    $ 295.00
    Regular Price
    $ 295.00
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    Washed Calfskin Bit Driver by Country Club Prep
    Regular Price
    $ 280.00
    Sale Price
    $ 280.00
    Regular Price
    $ 280.00
    Unit Price
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    Navy Camo Needlepoint Belgian Loafers by Smathers & Branson
    Regular Price
    $ 425.00
    Sale Price
    $ 425.00
    Regular Price
    $ 425.00
    Unit Price
    per 
    Kiawah Vail Bit Driver by Country Club Prep
    Regular Price
    $ 250.00
    Sale Price
    $ 250.00
    Regular Price
    $ 250.00
    Unit Price
    per 
    Key West Croco Combo Penny Loafer by Country Club Prep
    Regular Price
    $ 225.00
    Sale Price
    $ 225.00
    Regular Price
    $ 225.00
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    Dyed in the Wool Horse Bit Driver by Country Club Prep
    Regular Price
    $ 225.00
    Sale Price
    $ 225.00
    Regular Price
    $ 225.00
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    Lace Bit Driver by Country Club Prep
    Regular Price
    $ 220.00
    Sale Price
    $ 220.00
    Regular Price
    $ 220.00
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    Men's Authentic Original Boat Shoe in Brown Buc by Sperry
    Regular Price
    $ 95.00
    Sale Price
    $ 95.00
    Regular Price
    $ 95.00
    Unit Price
    per 
    SOLD OUT
    Santa Fe Panel Boot by Country Club Prep
    Regular Price
    $ 127.95
    Sale Price
    $ 127.95
    Regular Price
    $ 245.00
    Unit Price
    per 
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson
    Regular Price
    $ 425.00
    Sale Price
    $ 425.00
    Regular Price
    $ 425.00
    Unit Price
    per 
    Men's Avenue Duck Boot in Tan and Brown by Sperry
    Regular Price
    $ 99.95
    Sale Price
    $ 99.95
    Regular Price
    $ 99.95
    Unit Price
    per 
    Uncle Sam Needlepoint Belgian Loafers by Smathers & Branson
    Regular Price
    $ 425.00
    Sale Price
    $ 425.00
    Regular Price
    $ 425.00
    Unit Price
    per 
    Save 36%
    Woolly Croco Penny Loafer by Country Club Prep
    Regular Price
    $ 145.00
    Sale Price
    $ 145.00
    Regular Price
    $ 225.00
    Unit Price
    per 
    Ventura Sueded Calfskin Penny Loafer by Country Club Prep
    Regular Price
    $ 280.00
    Sale Price
    $ 280.00
    Regular Price
    $ 280.00
    Unit Price
    per 
    Preston Washed Calfskin Penny Loafer by Country Club Prep
    Regular Price
    $ 300.00
    Sale Price
    $ 300.00
    Regular Price
    $ 300.00
    Unit Price
    per 
    Men's Avenue Duck Boot in Black & Amaretto by Sperry
    Regular Price
    $ 99.95
    Sale Price
    $ 99.95
    Regular Price
    $ 99.95
    Unit Price
    per 
    Men's Billfish 3-Eye Boat Shoe in Tan and Beige by Sperry
    Regular Price
    $ 99.95
    Sale Price
    $ 99.95
    Regular Price
    $ 99.95
    Unit Price
    per 
    Save 48%
    Ashby Nubuck Slip On by Country Club Prep
    Regular Price
    $ 117.95
    Sale Price
    $ 117.95
    Regular Price
    $ 225.00
    Unit Price
    per 
    Save 44%
    Sueded Alligator Grain Horse Bit Driver by Country Club Prep
    Regular Price
    $ 125.00
    Sale Price
    $ 125.00
    Regular Price
    $ 225.00
    Unit Price
    per 

    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!