Country Club Prep Built to Last

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

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    Cotuit Madras Shorts by Country Club Prep - Country Club Prep
    Cotuit Madras Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Red Seersucker Shorts by Country Club Prep - Country Club Prep
    Red Seersucker Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Tan Seersucker Shorts by Country Club Prep - Country Club Prep
    Tan Seersucker Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Blue Seersucker Shorts by Country Club Prep - Country Club Prep
    Blue Seersucker Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Pastel Patchwork Madras Shorts by Country Club Prep - Country Club Prep
    Pastel Patchwork Madras Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Mini Gingham Shorts in Royal Blue by Country Club Prep - Country Club Prep
    Mini Gingham Shorts in Royal Blue by Country Club Prep
    $ 120.00
    $ 120.00

    Traditional Madras Shorts by Country Club Prep - Country Club Prep
    Traditional Madras Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Pink Seersucker Shorts by Country Club Prep - Country Club Prep
    Pink Seersucker Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Orange Seersucker Shorts by Country Club Prep - Country Club Prep
    Orange Seersucker Shorts by Country Club Prep
    $ 120.00
    $ 120.00

    Cisco Short in Weston Patch Madras by Castaway Clothing - Country Club Prep
    Cisco Short in Weston Patch Madras by Castaway Clothing
    $ 118.00
    $ 118.00
    Cisco Short in Chancellor Patch Madras by Castaway Clothing - Country Club Prep
    Cisco Short in Chancellor Patch Madras by Castaway Clothing
    $ 118.00
    $ 118.00

    Gingham Party Panel Cisco Short by Castaway Clothing - Country Club Prep
    Gingham Party Panel Cisco Short by Castaway Clothing
    $ 118.00
    $ 118.00
    $ 118.00
    Cisco Short in Hingham Patch Madras by Castaway Clothing - Country Club Prep
    Cisco Short in Hingham Patch Madras by Castaway Clothing
    $ 118.00
    $ 118.00

    Cisco Short in Osterville Patch Madras by Castaway Clothing - Country Club Prep
    Cisco Short in Osterville Patch Madras by Castaway Clothing
    $ 118.00
    $ 118.00
    Island Canvas Short with Tequila, Salt & Lime in Dark Denim by Castaway Clothing - Country Club Prep
    Island Canvas Short with Tequila, Salt & Lime in Dark Denim by Castaway Clothing
    $ 110.00
    $ 110.00
    $ 110.00
    Embroidered Cisco Shorts Blue Seersucker with Martini Glasses by Castaway Clothing - Country Club Prep
    Embroidered Cisco Shorts Blue Seersucker with Martini Glasses by Castaway Clothing
    $ 110.00
    $ 110.00

    Castle Harbor Stripe Sport Shirt in Coral Beach by Southern Tide - Country Club Prep
    Castle Harbor Stripe Sport Shirt in Coral Beach by Southern Tide
    $ 110.00
    $ 110.00

    Atlantic Plaid Sport Shirt in Royal Blue by Southern Tide - Country Club Prep
    Atlantic Plaid Sport Shirt in Royal Blue by Southern Tide
    $ 99.50
    $ 99.50
    Beaufain Plaid Sport Shirt in Sunset by Southern Tide - Country Club Prep
    Beaufain Plaid Sport Shirt in Sunset by Southern Tide
    $ 99.50
    $ 99.50

    Cisco Short with Embroidered Hangover Special by Castaway Clothing - Country Club Prep
    Cisco Short with Embroidered Hangover Special by Castaway Clothing
    $ 98.00
    $ 98.00

    Orange & Navy Oxford Stripe Suspenders/ Braces by High Cotton - Country Club Prep
    Orange & Navy Oxford Stripe Suspenders/ Braces by High Cotton
    $ 98.00
    $ 98.00
    Save 48%
    Isabel Grace Dress by Southern Tide - Country Club Prep
    Isabel Grace Dress by Southern Tide
    $ 97.95
    $ 97.95
    $ 188.00
    The Broad Street Linen Short by Country Club Prep - Country Club Prep
    The Broad Street Linen Short by Country Club Prep
    $ 95.00
    $ 95.00
    The Charlottesville Orange Pant by Country Club Prep - Country Club Prep
    The Charlottesville Orange Pant by Country Club Prep
    $ 95.00
    $ 95.00

    Limited Edition Longshanks Needlepoint Flask in Blue by Smathers & Branson - Country Club Prep
    Limited Edition Longshanks Needlepoint Flask in Blue by Smathers & Branson
    $ 95.00
    $ 95.00
    $ 95.00

    Tonal Seersucker Skipjack Short by Southern Tide - Country Club Prep
    Tonal Seersucker Skipjack Short by Southern Tide
    $ 89.50
    $ 89.50

    Save 48%
    Seersucker Fit and Flare Dress by Vineyard Vines - Country Club Prep
    Seersucker Fit and Flare Dress by Vineyard Vines
    $ 82.95
    $ 82.95
    $ 158.00
    The Merciful Marlin Resort Short by Country Club Prep - Country Club Prep
    The Merciful Marlin Resort Short by Country Club Prep
    $ 79.50
    $ 79.50
    Save 48%
    Chase Long Sleeve Shirt by Castaway Clothing - Country Club Prep
    Chase Long Sleeve Shirt by Castaway Clothing
    $ 76.95
    $ 76.95
    $ 148.00
    Save 48%
    Linen Pants in Stone by Country Club Prep - Country Club Prep
    Linen Pants in Stone by Country Club Prep
    $ 75.95
    $ 75.95
    $ 145.00
    And They're Off! Silk Fabric Cufflinks in Red by Bird Dog Bay - Country Club Prep
    And They're Off! Silk Fabric Cufflinks in Red by Bird Dog Bay
    $ 75.00
    $ 75.00
    Save 47%
    Plain Front Pants in Faded Red by Country Club Prep - Country Club Prep
    Plain Front Pants in Faded Red by Country Club Prep
    $ 70.95
    $ 70.95
    $ 135.00

    Seersucker Soiree Leather Tab Belt on Navy Canvas by Country Club Prep - Country Club Prep
    Seersucker Soiree Leather Tab Belt on Navy Canvas by Country Club Prep
    $ 69.50
    $ 69.50
    $ 69.50

    Old Glory Leather Tab Belt on Blue Seersucker by Country Club Prep - Country Club Prep
    Old Glory Leather Tab Belt on Blue Seersucker by Country Club Prep
    $ 69.50
    $ 69.50
    $ 69.50
    Darlin Valentino Bracelet by Kiel James Patrick - Country Club Prep
    Darlin Valentino Bracelet by Kiel James Patrick
    $ 68.00
    $ 68.00
    Horseshoe Needlepoint Credit Card Wallet by Smathers & Branson - Country Club Prep
    Horseshoe Needlepoint Credit Card Wallet by Smathers & Branson
    $ 65.00
    $ 65.00
    $ 65.00

    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!