Country Club Prep Built to Last

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

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    Jolly Roger Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Jolly Roger Needlepoint Belgian Loafers by Smathers & Branson
    $ 395.00
    $ 395.00
    $ 425.00
    Save 7%
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Herringbone Needlepoint Belgian Loafers by Smathers & Branson
    $ 395.00
    $ 395.00
    $ 425.00
    Save 7%
    Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson
    $ 395.00
    $ 395.00
    $ 425.00

    Save 7%
    Navy Camo Needlepoint Belgian Loafers by Smathers & Branson - Country Club Prep
    Navy Camo Needlepoint Belgian Loafers by Smathers & Branson
    $ 395.00
    $ 395.00
    $ 425.00
    Spinnaker Blazer in Osterville Patch Madras by Castaway Clothing - Country Club Prep
    Spinnaker Blazer in Osterville Patch Madras by Castaway Clothing
    $ 345.00
    $ 345.00
    $ 345.00
    Spinnaker Blazer With Embroidered White Anchor in Blue Grotto by Castaway Clothing - Country Club Prep
    Spinnaker Blazer With Embroidered White Anchor in Blue Grotto by Castaway Clothing
    $ 325.00
    $ 325.00
    $ 325.00
    Spinnaker Blazer With Embroidered White Anchor in Seagrass by Castaway Clothing - Country Club Prep
    Spinnaker Blazer With Embroidered White Anchor in Seagrass by Castaway Clothing
    $ 325.00
    $ 325.00
    $ 325.00
    Navy & Red Surcingle Downing Bit Loafer in Espresso Suede by Smathers & Branson - Country Club Prep
    Navy & Red Surcingle Downing Bit Loafer in Espresso Suede by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    Navy & Pink Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson - Country Club Prep
    Navy & Pink Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    Navy & Red Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson - Country Club Prep
    Navy & Red Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    American Flag Downing Bit Loafer by Smathers & Branson - Country Club Prep
    American Flag Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    Navy Camo Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Navy Camo Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00
    Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    Navy & Red Surcingle Downing Bit Loafer by Smathers & Branson - Country Club Prep
    Navy & Red Surcingle Downing Bit Loafer by Smathers & Branson
    $ 295.00
    $ 295.00
    $ 295.00

    Fox Fields Dress in Shell Fan by Elizabeth McKay - Country Club Prep
    Fox Fields Dress in Shell Fan by Elizabeth McKay
    $ 285.00
    $ 285.00
    Long Sleeve Flare Fringe Tunic Dress by Sail to Sable - Country Club Prep
    Long Sleeve Flare Fringe Tunic Dress by Sail to Sable
    $ 248.00
    $ 248.00
    Navy & Forest Surcingle Needlepoint Driving Shoe in Smoke Suede by Smathers & Branson - Country Club Prep
    Navy & Forest Surcingle Needlepoint Driving Shoe in Smoke Suede by Smathers & Branson
    $ 245.00
    $ 245.00
    $ 245.00
    Navy & Red Surcingle Needlepoint Driving Shoe in Cognac Suede by Smathers & Branson - Country Club Prep
    Navy & Red Surcingle Needlepoint Driving Shoe in Cognac Suede by Smathers & Branson
    $ 245.00
    $ 245.00
    $ 245.00
    University of Georgia Surcingle Needlepoint Driving Shoes by Smathers & Branson - Country Club Prep
    University of Georgia Surcingle Needlepoint Driving Shoes by Smathers & Branson
    $ 245.00
    $ 245.00
    $ 245.00

    Save 11%
    Classic White Suede Sport Buck by Country Club Prep - Country Club Prep
    Classic White Suede Sport Buck by Country Club Prep
    $ 245.00
    $ 245.00
    $ 275.00

    University of Alabama Surcingle Needlepoint Driving Shoes by Smathers & Branson - Country Club Prep
    University of Alabama Surcingle Needlepoint Driving Shoes by Smathers & Branson
    $ 245.00
    $ 245.00
    $ 245.00

    Surcingle Needlepoint Driving Shoes by Smathers & Branson - Country Club Prep
    Surcingle Needlepoint Driving Shoes by Smathers & Branson
    $ 245.00
    $ 245.00
    $ 245.00

    Dyed in the Wool Horse Bit Driver by Country Club Prep - Country Club Prep
    Dyed in the Wool Horse Bit Driver by Country Club Prep
    $ 225.00
    $ 225.00
    $ 225.00
    Save 13%
    Men's Bit by a Croc Driving Shoes by Country Club Prep - Country Club Prep
    Men's Bit by a Croc Driving Shoes by Country Club Prep
    $ 195.00
    $ 195.00
    $ 225.00

    Save 13%
    Men's Young Partner Driving Shoes in Gridiron Brown by Country Club Prep - Country Club Prep
    Men's Young Partner Driving Shoes in Gridiron Brown by Country Club Prep
    $ 195.00
    $ 195.00
    $ 225.00

    Save 13%
    Men's Young Partner Bit Driving Shoes in Briar Waxy with Off-White Stitching by Country Club Prep - Country Club Prep
    Men's Young Partner Bit Driving Shoes in Briar Waxy with Off-White Stitching by Country Club Prep
    $ 195.00
    $ 195.00
    $ 225.00

    Save 13%
    Men's Young Partner Bit Driving Shoes in Black Waxy with Matching Stitching by Country Club Prep - Country Club Prep
    Men's Young Partner Bit Driving Shoes in Black Waxy with Matching Stitching by Country Club Prep
    $ 195.00
    $ 195.00
    $ 225.00

    Horseshoe Needlepoint Belt by Smathers & Branson - Country Club Prep
    Horseshoe Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 195.00
    Fox Chase Needlepoint Belt by Smathers & Branson - Country Club Prep
    Fox Chase Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00

    Country Club Prep Madras Plaid Needlepoint Belt by Smathers & Branson - Country Club Prep
    Country Club Prep Madras Plaid Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00

    Bourbon Bottles Needlepoint Belt by Smathers & Branson - Country Club Prep
    Bourbon Bottles Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00

    Kentucky Derby Life Needlepoint Belt by Smathers & Branson - Country Club Prep
    Kentucky Derby Life Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00

    University of Kentucky SEC Seal Needlepoint Belt by Smathers & Branson - Country Club Prep
    University of Kentucky SEC Seal Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00
    Lexington KY Custom Title Town Needlepoint Belt by Smathers & Branson - Country Club Prep
    Lexington KY Custom Title Town Needlepoint Belt by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00

    Morning Buzz Needlepoint Belt in Classic Navy by Smathers & Branson - Country Club Prep
    Morning Buzz Needlepoint Belt in Classic Navy by Smathers & Branson
    $ 195.00
    $ 195.00
    $ 185.00
    Vanessa Raffia Wedge in Gold by Jack Rogers - Country Club Prep
    Vanessa Raffia Wedge in Gold by Jack Rogers
    $ 178.00
    $ 178.00

    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!