Popular Preppy Clothing for Women & Men

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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
    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
    Save 48%
    Sherpa Fleece Booties by Nordic Fleece - Country Club Prep
    Sherpa Fleece Booties by Nordic Fleece
    $ 25.95
    $ 25.95
    $ 49.99
    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
    SOLD OUT
    Men's Kerry Boot by Dubarry of Ireland - Country Club Prep
    Men's Kerry Boot by Dubarry of Ireland
    $ 379.00
    $ 379.00
    $ 379.00
    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
    Men's Authentic Original Boat Shoe in Sahara by Sperry - Country Club Prep
    Men's Authentic Original Boat Shoe in Sahara by Sperry
    $ 95.00
    $ 95.00
    $ 95.00
    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
    SOLD OUT
    Santa Fe Panel Boot by Country Club Prep - Country Club Prep
    Santa Fe Panel Boot by Country Club Prep
    $ 127.95
    $ 127.95
    $ 245.00
    Oslo Leopard Sherpa Booties by Nordic Fleece - Country Club Prep
    Oslo Leopard Sherpa Booties by Nordic Fleece
    $ 49.99
    $ 49.99
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson
    $ 425.00
    $ 425.00
    $ 425.00
    Halden Faux Fur Slippers by Nordic Fleece - Country Club Prep
    Halden Faux Fur Slippers by Nordic Fleece
    $ 58.00
    $ 58.00
    Men's Avenue Duck Boot in Tan and Brown by Sperry - Country Club Prep
    Men's Avenue Duck Boot in Tan and Brown by Sperry
    $ 99.95
    $ 99.95
    $ 99.95
    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
    Bow Booties by Nordic Fleece - Country Club Prep
    Bow Booties by Nordic Fleece
    $ 49.99
    $ 49.99
    Save 47%
    Lower King Boot by Charleston Shoe Co. - Country Club Prep
    Lower King Boot by Charleston Shoe Co.
    $ 78.95
    $ 78.95
    $ 150.00
    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
    SOLD OUT
    Antrim Boot by Dubarry of Ireland - Country Club Prep
    Antrim Boot by Dubarry of Ireland
    $ 299.00
    $ 299.00
    $ 299.00
    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
    Men's Gold Cup A/O 2 Eye Boat Shoe in Dark Tan by Sperry - Country Club Prep
    Men's Gold Cup A/O 2 Eye Boat Shoe in Dark Tan by Sperry
    $ 160.00
    $ 160.00
    $ 160.00
    Pearl Bow Fleece Booties by Nordic Fleece - Country Club Prep
    Pearl Bow Fleece Booties by Nordic Fleece
    $ 49.99
    $ 49.99
    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
    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
    Jacks Haircalf Flat Sandal by Jack Rogers - Country Club Prep
    Jacks Haircalf Flat Sandal by Jack Rogers
    $ 138.00
    $ 138.00

    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!