Popular Preppy Clothing for Women & Men

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    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
    Tassel Sherpa Fleece Booties by Nordic Fleece - Country Club Prep
    Tassel Sherpa Fleece Booties by Nordic Fleece
    $ 49.99
    $ 49.99
    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
    Millie Suede Moccasin by Jack Rogers - Country Club Prep
    Millie Suede Moccasin by Jack Rogers
    $ 128.00
    $ 128.00
    $ 128.00
    Men's Billfish 3-Eye Boat Shoe in Tan and Beige by Sperry - Country Club Prep
    Men's Billfish 3-Eye Boat Shoe in Tan and Beige by Sperry
    $ 99.95
    $ 99.95
    $ 99.95
    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
    Women's Bailey Button II Boot by UGG - Country Club Prep
    Women's Bailey Button II Boot by UGG
    $ 170.00
    $ 170.00
    SOLD OUT
    Women's Classic Mini II Boot by UGG - Country Club Prep
    Women's Classic Mini II Boot by UGG
    $ 140.00
    $ 140.00
    SOLD OUT
    Men's Dancing Bears Needlepoint Flip Flops in Dark Navy by Smathers & Branson - Country Club Prep
    Men's Dancing Bears Needlepoint Flip Flops in Dark Navy by Smathers & Branson
    $ 89.50
    $ 89.50
    SOLD OUT
    Men's Beachside Flipjacks in Royal Blue by Southern Tide - Country Club Prep
    Men's Beachside Flipjacks in Royal Blue by Southern Tide
    $ 69.50
    $ 69.50
    SOLD OUT
    Sherpa Fleece Booties in Island Reef and Oatmeal by Live Oak - Country Club Prep
    Sherpa Fleece Booties in Island Reef and Oatmeal by Live Oak
    $ 55.00
    $ 55.00
    SOLD OUT
    Women's Classic Short II Boot by UGG - Country Club Prep
    Women's Classic Short II Boot by UGG
    $ 160.00
    $ 160.00
    SOLD OUT
    Men's Limited Edition Madras Needlepoint Flip Flops by Smathers & Branson - Country Club Prep
    Men's Limited Edition Madras Needlepoint Flip Flops by Smathers & Branson
    $ 89.50
    $ 89.50
    SOLD OUT
    Men's Stars and Stripes Needlepoint Flip Flops by Smathers & Branson - Country Club Prep
    Men's Stars and Stripes Needlepoint Flip Flops by Smathers & Branson
    $ 89.50
    $ 89.50
    SOLD OUT
    Men's Carter Stripe Needlepoint Flip Flops by Smathers & Branson - Country Club Prep
    Men's Carter Stripe Needlepoint Flip Flops by Smathers & Branson
    $ 89.50
    $ 89.50
    SOLD OUT
    Women's Adirondack Fluff Boot III by UGG - Country Club Prep
    Women's Adirondack Fluff Boot III by UGG
    $ 250.00
    $ 250.00
    SOLD OUT
    Men's Cold Bay Chukka Boot by Sperry - Country Club Prep
    Men's Cold Bay Chukka Boot by Sperry
    $ 109.95
    $ 109.95
    $ 109.95
    SOLD OUT
    Women's Original Play Tall Rain Boots by Hunter - Country Club Prep
    Women's Original Play Tall Rain Boots by Hunter
    $ 110.00
    $ 110.00
    SOLD OUT
    Women's Crest Vibe Sneaker in Oat by Sperry - Country Club Prep
    Women's Crest Vibe Sneaker in Oat by Sperry
    $ 29.99
    $ 29.99
    $ 59.95
    SOLD OUT
    Sherpa Fleece Booties in Oatmeal and Charcoal by Live Oak - Country Club Prep
    Sherpa Fleece Booties in Oatmeal and Charcoal by Live Oak
    $ 55.00
    $ 55.00
    SOLD OUT
    Men's Neumel Boot by UGG - Country Club Prep
    Men's Neumel Boot by UGG
    $ 130.00
    $ 130.00
    SOLD OUT
    Men's Nautical Alphabet Needle Point Flip Flops in Tan Leather by Smathers & Branson - Country Club Prep
    Men's Nautical Alphabet Needle Point Flip Flops in Tan Leather by Smathers & Branson
    $ 89.50
    $ 89.50
    SOLD OUT
    Women's Saltwater 2-Eye Plaid Wool Duck Boot by Sperry - Country Club Prep
    Women's Saltwater 2-Eye Plaid Wool Duck Boot by Sperry
    $ 99.95
    $ 99.95
    $ 99.95
    SOLD OUT
    Men's Authentic Original Tailored Boat Shoe by Sperry - Country Club Prep
    Men's Authentic Original Tailored Boat Shoe by Sperry
    $ 49.99
    $ 49.99
    $ 84.95
    SOLD OUT
    Women's Original Insulated Roll Top Sherpa Boots by Hunter - Country Club Prep
    Women's Original Insulated Roll Top Sherpa Boots by Hunter
    $ 125.00
    $ 125.00
    SOLD OUT
    Women's Original Short Rain Boots by Hunter - Country Club Prep
    Women's Original Short Rain Boots by Hunter
    $ 140.00
    $ 140.00
    SOLD OUT
    Rainwell Short Slip-On Rain Boots in French Navy by Joules - Country Club Prep
    Rainwell Short Slip-On Rain Boots in French Navy by Joules
    $ 69.95
    $ 69.95
    $ 69.95
    SOLD OUT
    Millie Haircalf Moccasin by Jack Rogers - Country Club Prep
    Millie Haircalf Moccasin by Jack Rogers
    $ 148.00
    $ 148.00
    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
    Men's Dockside Leather Upper Flipjacks in Dress Blues by Southern Tide - Country Club Prep
    Men's Dockside Leather Upper Flipjacks in Dress Blues by Southern Tide
    $ 59.50
    $ 59.50
    SOLD OUT
    Men's Ascot Slipper by UGG - Country Club Prep
    Men's Ascot Slipper by UGG
    $ 110.00
    $ 110.00
    SOLD OUT
    Men's Dockside Leather Upper Flipjacks in Dark Brown by Southern Tide - Country Club Prep
    Men's Dockside Leather Upper Flipjacks in Dark Brown by Southern Tide
    $ 59.50
    $ 59.50
    SOLD OUT
    Morris Wingtip Oxford by Cole Haan - Country Club Prep
    Morris Wingtip Oxford by Cole Haan
    $ 104.95
    $ 104.95
    $ 200.00

    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!