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
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$ 395.00
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$ 395.00
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$ 425.00
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Herringbone Needlepoint Belgian Loafers by Smathers & Branson
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$ 395.00
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$ 395.00
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$ 425.00
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Save 7%
Dancing Bears Needlepoint Belgian Loafers by Smathers & Branson
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$ 395.00
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$ 395.00
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$ 425.00
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1 total reviews

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Navy Camo Needlepoint Belgian Loafers by Smathers & Branson
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$ 395.00
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$ 395.00
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$ 425.00
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Spinnaker Blazer in Osterville Patch Madras by Castaway Clothing
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$ 345.00
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$ 345.00
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$ 345.00
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Spinnaker Blazer With Embroidered White Anchor in Blue Grotto by Castaway Clothing
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$ 325.00
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$ 325.00
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$ 325.00
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Spinnaker Blazer With Embroidered White Anchor in Seagrass by Castaway Clothing
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$ 325.00
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$ 325.00
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$ 325.00
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Dancing Bears Downing Bit Loafer by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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2 total reviews

Navy & Red Surcingle Downing Bit Loafer in Espresso Suede by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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2 total reviews

Navy & Pink Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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2 total reviews

Navy & Red Surcingle Downing Bit Loafer in Saddle Leather by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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1 total reviews

American Flag Downing Bit Loafer by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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9 total reviews

Navy Camo Downing Bit Loafer by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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Light Blue Darcy Stripe Downing Bit Loafer by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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7 total reviews

Navy & Red Surcingle Downing Bit Loafer by Smathers & Branson
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$ 295.00
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$ 295.00
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$ 295.00
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3 total reviews

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

Save 11%
Classic White Suede Sport Buck by Country Club Prep
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$ 245.00
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$ 245.00
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$ 275.00
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12 total reviews

University of Alabama Surcingle Needlepoint Driving Shoes by Smathers & Branson
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$ 245.00
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$ 245.00
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$ 245.00
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1 total reviews

Surcingle Needlepoint Driving Shoes by Smathers & Branson
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$ 245.00
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$ 245.00
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$ 245.00
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1 total reviews

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

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

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

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

Horseshoe Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 195.00
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Fox Chase Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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1 total reviews

Country Club Prep Madras Plaid Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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1 total reviews

Bourbon Bottles Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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1 total reviews

Kentucky Derby Life Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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1 total reviews

University of Kentucky SEC Seal Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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Lexington KY Custom Title Town Needlepoint Belt by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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1 total reviews

Morning Buzz Needlepoint Belt in Classic Navy by Smathers & Branson
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$ 195.00
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$ 195.00
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$ 185.00
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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!