Popular Preppy Clothing for Women & Men

122 products

Filter by

    SOLD OUT
    Men's Avenue Winter Duck Boot in Brown & Black by Sperry
    Regular Price
    $ 109.95
    Sale Price
    $ 109.95
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Sundance Bison Driver by Country Club Prep
    Regular Price
    $ 145.00
    Sale Price
    $ 145.00
    Regular Price
    $ 245.00
    Unit Price
    per 
    SOLD OUT
    Women's Original Insulated Sherpa Shoe by Hunter
    Regular Price
    $ 95.00
    Sale Price
    $ 95.00
    Regular Price
    Unit Price
    per 
    SOLD OUT
    ZERØGRAND All-Day Trainer by Cole Haan
    Regular Price
    $ 114.95
    Sale Price
    $ 114.95
    Regular Price
    $ 220.00
    Unit Price
    per 
    SOLD OUT
    Men's Shamrock Needlepoint Flip Flops in Dark Navy by Smathers & Branson
    Regular Price
    $ 89.50
    Sale Price
    $ 89.50
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Men's Longshanks Needle Point Flip Flops in Navy by Smathers & Branson
    Regular Price
    $ 89.50
    Sale Price
    $ 89.50
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Men's Authentic Original Boat Shoe in Navy by Sperry
    Regular Price
    $ 95.00
    Sale Price
    $ 95.00
    Regular Price
    $ 95.00
    Unit Price
    per 
    SOLD OUT
    Men's 19th Hole Needle Point Flip Flops in Navy by Smathers & Branson
    Regular Price
    $ 89.50
    Sale Price
    $ 89.50
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Men's Old Glory Needlepoint Flip Flops in Red White and Blue by Smathers & Branson
    Regular Price
    $ 89.50
    Sale Price
    $ 89.50
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Sherpa Fleece Booties in Cranberry and Oatmeal by Live Oak
    Regular Price
    $ 55.00
    Sale Price
    $ 55.00
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Women's Original Tall Rain Boots by Hunter
    Regular Price
    $ 150.00
    Sale Price
    $ 150.00
    Regular Price
    Unit Price
    per 
    SOLD OUT
    ØriginalGrand Wingtip Oxford by Cole Haan
    Regular Price
    $ 150.00
    Sale Price
    $ 150.00
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Men's UGA Needle Point Flip Flops in Tan Leather by Smathers & Branson
    Regular Price
    $ 89.50
    Sale Price
    $ 89.50
    Regular Price
    Unit Price
    per 
    SOLD OUT
    Women's Original Short Back Adjustable Rain Boots by Hunter
    Regular Price
    $ 150.00
    Sale Price
    $ 150.00
    Regular Price
    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!