Popular Preppy Clothing for Women & Men

19 products

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    Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00
    Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson
    $ 425.00
    $ 425.00
    $ 425.00
    Dancing Bears Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Dancing Bears Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00
    Save 39%
    Dapper Ribbon Bit Driving Shoes by Country Club Prep - Country Club Prep
    Dapper Ribbon Bit Driving Shoes by Country Club Prep
    $ 159.00
    $ 159.00
    $ 260.00
    Navy Camo Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Navy Camo Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00
    Navy Camo Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Navy Camo Needlepoint Belgian Loafers by Smathers & Branson
    $ 425.00
    $ 425.00
    $ 425.00
    Key West Croco Combo Penny Loafer by Country Club Prep - Country Club Prep
    Key West Croco Combo Penny Loafer by Country Club Prep
    $ 225.00
    $ 225.00
    $ 225.00
    Men's Authentic Original Boat Shoe in Brown Buc by Sperry - Country Club Prep
    Men's Authentic Original Boat Shoe in Brown Buc by Sperry
    $ 95.00
    $ 95.00
    $ 95.00
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson
    $ 425.00
    $ 425.00
    $ 425.00
    SOLD OUT
    Men's Authentic Original Plush Corduroy Boat Shoe by Sperry - Country Club Prep
    Men's Authentic Original Plush Corduroy Boat Shoe by Sperry
    $ 59.99
    $ 59.99
    $ 99.95
    Uncle Sam Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Uncle Sam Needlepoint Belgian Loafers by Smathers & Branson
    $ 425.00
    $ 425.00
    $ 425.00
    SOLD OUT
    Middleton Ankle Bootie by Charleston Shoe Co. - Country Club Prep
    Middleton Ankle Bootie by Charleston Shoe Co.
    $ 85.95
    $ 85.95
    $ 165.00
    Men's Avenue Duck Boot in Black & Amaretto by Sperry - Country Club Prep
    Men's Avenue Duck Boot in Black & Amaretto by Sperry
    $ 99.95
    $ 99.95
    $ 99.95
    SOLD OUT
    Men's Authentic Original Boat Shoe in Tan by Sperry - Country Club Prep
    Men's Authentic Original Boat Shoe in Tan by Sperry
    $ 95.00
    $ 95.00
    $ 95.00
    Millie Leather Moccasin by Jack Rogers - Country Club Prep
    Millie Leather Moccasin by Jack Rogers
    $ 128.00
    $ 128.00
    Save 44%
    Sueded Alligator Grain Horse Bit Driver by Country Club Prep - Country Club Prep
    Sueded Alligator Grain Horse Bit Driver by Country Club Prep
    $ 125.00
    $ 125.00
    $ 225.00
    SOLD OUT
    Cassity Elk Driver in Mahogany by Country Club Prep - Country Club Prep
    Cassity Elk Driver in Mahogany by Country Club Prep
    $ 195.00
    $ 195.00
    $ 295.00
    SOLD OUT
    Women's Fluff Yeah Slide by UGG - Country Club Prep
    Women's Fluff Yeah Slide by UGG
    $ 100.00
    $ 100.00
    SOLD OUT
    Men's Authentic Original Boat Shoe in Navy by Sperry - Country Club Prep
    Men's Authentic Original Boat Shoe in Navy by Sperry
    $ 95.00
    $ 95.00
    $ 95.00

    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!