Country Club Prep Built to Last

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

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Vanessa Raffia Wedge in Gold by Jack Rogers
Regular Price
$ 178.00
Sale Price
$ 178.00
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Stretch Twill Harbor Pant in Liberty with Embroidered Racing Horses by Castaway Clothing
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$ 165.00
Sale Price
$ 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
Sale Price
$ 158.00
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Save 48%
Sophia Dress in Coral by Camilyn Beth
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$ 148.95
Sale Price
$ 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
Regular Price
$ 148.00
Sale Price
$ 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
Sale Price
$ 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
Regular Price
$ 148.00
Sale Price
$ 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
Sale Price
$ 145.00
Regular Price
$ 145.00
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5 total reviews

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

New Pastel Madras Pants by Country Club Prep
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$ 145.00
Sale Price
$ 145.00
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Cotuit Madras Pants by Country Club Prep
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$ 145.00
Sale Price
$ 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
Sale Price
$ 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
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$ 145.00
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$ 145.00
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Pastel Madras Pants by Country Club Prep
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$ 145.00
Sale Price
$ 145.00
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15 total reviews

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

Derby Blue Seersucker Pants by Country Club Prep
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$ 135.00
Sale Price
$ 135.00
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$ 135.00
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per 

7 total reviews

Pink Seersucker Pants by Country Club Prep
Regular Price
$ 135.00
Sale Price
$ 135.00
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$ 135.00
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per 

2 total reviews

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

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

Hamptons Jack Sandal in Silver by Jack Rogers
Regular Price
$ 128.00
Sale Price
$ 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

Save 48%
Bouvier Dress in Hot Pink by Elizabeth McKay
Regular Price
$ 127.95
Sale Price
$ 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
Sale Price
$ 125.00
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1 total reviews

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

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

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

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

Vineyard Madras Shorts by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
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2 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!