Popular Preppy Clothing for Women & Men

23 products

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    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
    SOLD OUT
    Preston Deerskin Tassel Loafer by Country Club Prep - Country Club Prep
    Preston Deerskin Tassel Loafer by Country Club Prep
    $ 320.00
    $ 320.00
    $ 320.00
    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
    Washed Calfskin Bit Driver by Country Club Prep - Country Club Prep
    Washed Calfskin Bit Driver by Country Club Prep
    $ 280.00
    $ 280.00
    $ 280.00
    SOLD OUT
    Ventura Sheepskin Horse Bit Loafer by Country Club Prep - Country Club Prep
    Ventura Sheepskin Horse Bit Loafer by Country Club Prep
    $ 260.00
    $ 260.00
    $ 260.00
    SOLD OUT
    Ventura Deerskin Penny Loafer by Country Club Prep - Country Club Prep
    Ventura Deerskin Penny Loafer by Country Club Prep
    $ 275.00
    $ 275.00
    $ 275.00
    Kiawah Vail Bit Driver by Country Club Prep - Country Club Prep
    Kiawah Vail Bit Driver by Country Club Prep
    $ 250.00
    $ 250.00
    $ 250.00
    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
    Dyed in the Wool Horse Bit Driver by Country Club Prep - Country Club Prep
    Dyed in the Wool Horse Bit Driver by Country Club Prep
    $ 225.00
    $ 225.00
    $ 225.00
    Lace Bit Driver by Country Club Prep - Country Club Prep
    Lace Bit Driver by Country Club Prep
    $ 220.00
    $ 220.00
    $ 220.00
    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
    SOLD OUT
    Ashby Bison Slip On by Country Club Prep - Country Club Prep
    Ashby Bison Slip On by Country Club Prep
    $ 127.95
    $ 127.95
    $ 245.00
    Save 36%
    Woolly Croco Penny Loafer by Country Club Prep - Country Club Prep
    Woolly Croco Penny Loafer by Country Club Prep
    $ 145.00
    $ 145.00
    $ 225.00
    Ventura Sueded Calfskin Penny Loafer by Country Club Prep - Country Club Prep
    Ventura Sueded Calfskin Penny Loafer by Country Club Prep
    $ 280.00
    $ 280.00
    $ 280.00
    SOLD OUT
    Men's Authentic Original Boat Shoe in Classic Brown by Sperry - Country Club Prep
    Men's Authentic Original Boat Shoe in Classic Brown by Sperry
    $ 95.00
    $ 95.00
    $ 95.00
    Preston Washed Calfskin Penny Loafer by Country Club Prep - Country Club Prep
    Preston Washed Calfskin Penny Loafer by Country Club Prep
    $ 300.00
    $ 300.00
    $ 300.00
    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
    Save 48%
    Ashby Nubuck Slip On by Country Club Prep - Country Club Prep
    Ashby Nubuck Slip On by Country Club Prep
    $ 117.95
    $ 117.95
    $ 225.00
    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
    Morris Wingtip Oxford by Cole Haan - Country Club Prep
    Morris Wingtip Oxford by Cole Haan
    $ 104.95
    $ 104.95
    $ 200.00
    SOLD OUT
    Men's Gold Cup Authentic Original Boat Shoe in Navy/White by Sperry - Country Club Prep
    Men's Gold Cup Authentic Original Boat Shoe in Navy/White by Sperry
    $ 159.95
    $ 159.95
    $ 159.95
    SOLD OUT
    ZERØGRAND All-Day Trainer by Cole Haan - Country Club Prep
    ZERØGRAND All-Day Trainer by Cole Haan
    $ 114.95
    $ 114.95
    $ 220.00

    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!