Country Club Prep Built to Last

Derby Day Styles 2026: What to Wear to the Kentucky Derby

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    Stretch Twill Harbor Pant in Liberty with Embroidered Racing Horses by Castaway Clothing
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    $ 165.00
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    $ 165.00
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    $ 165.00
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    2 total reviews

    French Terry Short Sleeve Dress by Sail to Sable
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    $ 158.00
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    $ 158.00
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    Sophia Dress in Coral by Camilyn Beth
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    $ 148.95
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    $ 148.95
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    $ 285.00
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    2 total reviews

    Stretch Twill Harbor Pant with Embroidered Jockey Silks in Pink by Castaway Clothing
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    $ 148.00
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    $ 148.00
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    1 total reviews

    Stretch Twill Harbor Pant with Martini and Shaker by Castaway Clothing
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    $ 148.00
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    $ 148.00
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    Stretch Twill Harbor Pant with Embroidered Lucky Mint Julep in White by Castaway Clothing
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    $ 148.00
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    $ 148.00
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    Whisper Light Ruffle Hem Sweet Heart Dress by French Connection
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    $ 148.00
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    $ 148.00
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    $ 148.00
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    1 total reviews

    Vineyard Madras Pants by Country Club Prep
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    $ 145.00
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    $ 145.00
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    $ 145.00
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    5 total reviews

    Montauk Madras Pants by Country Club Prep
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    $ 145.00
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    $ 145.00
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    2 total reviews

    New Pastel Madras Pants by Country Club Prep
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    $ 145.00
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    $ 145.00
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    Cotuit Madras Pants by Country Club Prep
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    $ 145.00
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    $ 145.00
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    $ 145.00
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    Sunset Madras Pants by Country Club Prep
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    $ 145.00
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    $ 145.00
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    $ 145.00
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    4 total reviews

    Rugby Plain-front Pant in White Linen by Country Club Prep
    Regular Price
    $ 145.00
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    $ 145.00
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    Pastel Madras Pants by Country Club Prep
    Regular Price
    $ 145.00
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    $ 145.00
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    15 total reviews

    Traditional Madras Pants by Country Club Prep
    Regular Price
    $ 145.00
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    $ 145.00
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    23 total reviews

    Derby Blue Seersucker Pants by Country Club Prep
    Regular Price
    $ 135.00
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    $ 135.00
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    $ 135.00
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    7 total reviews

    Pink Seersucker Pants by Country Club Prep
    Regular Price
    $ 135.00
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    $ 135.00
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    $ 135.00
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    2 total reviews

    Tan Seersucker Pants by Country Club Prep
    Regular Price
    $ 135.00
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    $ 135.00
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    $ 135.00
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    2 total reviews

    Red Seersucker Pants by Country Club Prep
    Regular Price
    $ 135.00
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    $ 135.00
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    $ 135.00
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    1 total reviews

    Orange Seersucker Pants by Country Club Prep
    Regular Price
    $ 135.00
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    $ 135.00
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    $ 135.00
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    1 total reviews

    The Grantham Dress Shirt by Bird Dog Bay
    Regular Price
    $ 135.00
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    $ 135.00
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    Cisco Short in Bromley Patch Madras by Castaway Clothing
    Regular Price
    $ 128.00
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    $ 128.00
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    $ 128.00
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    Tinsley Demi Wedge by Jack Rogers
    Regular Price
    $ 128.00
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    $ 128.00
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    Palm Beach Jack Sandal in White by Jack Rogers
    Regular Price
    $ 128.00
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    $ 128.00
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    8 total reviews

    Hamptons Jack Sandal in Silver by Jack Rogers
    Regular Price
    $ 128.00
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    $ 128.00
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    6 total reviews

    Hamptons Jack Sandal in Gold by Jack Rogers
    Regular Price
    $ 128.00
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    $ 128.00
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    32 total reviews

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    Bouvier Dress in Hot Pink by Elizabeth McKay
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    $ 127.95
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    $ 127.95
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    $ 245.00
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    Mainstay Plaid Brrrº Intercoastal Performance Shirt by Southern Tide
    Regular Price
    $ 125.00
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    $ 125.00
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    1 total reviews

    Trim Fit Skipjack Pants in Kiwi by Southern Tide
    Regular Price
    $ 125.00
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    $ 125.00
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    Trim Fit Skipjack Pants in Fusion Coral by Southern Tide
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    $ 125.00
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    $ 125.00
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    Skipjack Classic Fit Pant in Stone by Southern Tide
    Regular Price
    $ 125.00
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    $ 125.00
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    1 total reviews

    Skipjack Classic Fit Pant in Sandstone Khaki by Southern Tide
    Regular Price
    $ 125.00
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    $ 125.00
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    3 total reviews

    S.N.O.B. Madras Shorts by Country Club Prep
    Regular Price
    $ 120.00
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    $ 120.00
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    2 total reviews

    New Pastel Madras Shorts by Country Club Prep
    Regular Price
    $ 120.00
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    $ 120.00
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    1 total reviews

    Vineyard Madras Shorts by Country Club Prep
    Regular Price
    $ 120.00
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    $ 120.00
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    2 total reviews

    Montauk Madras Shorts by Country Club Prep
    Regular Price
    $ 120.00
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    $ 120.00
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    8 total reviews

    The Kentucky Derby may be the "Fastest Two Minutes in Sports," but the parties and the memories last a lifetime. We're here to help you dress for the occasion with preppy seersucker jackets and dresses, outstanding madras bow ties, Jack Rogers flats and heels, and everything in between. Not going to a party this year? Pick up a Derby tee!