Derby Day Styles 2022: What to Wear to the Kentucky Derby

139 products

Filter by

Mini Gingham Shorts in Royal Blue by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
Regular Price
Unit Price
per 
Traditional Madras Shorts by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
Regular Price
Unit Price
per 
Pink Seersucker Shorts by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
Regular Price
Unit Price
per 
Orange Seersucker Shorts by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
Regular Price
Unit Price
per 
Cisco Short in Weston Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
Unit Price
per 
Cisco Short in Chancellor Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
Unit Price
per 
Gingham Party Panel Cisco Short by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
$ 118.00
Unit Price
per 
Cisco Short in Hingham Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
Unit Price
per 
Cisco Short in Osterville Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
Unit Price
per 
Napa Valley Jack Sandal in Cork and Gold by Jack Rogers
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
Unit Price
per 
Causeway Gingham Intercoastal Performance Shirt by Southern Tide
Regular Price
$ 115.00
Sale Price
$ 115.00
Regular Price
Unit Price
per 
Stretch Twill Cisco Short with Embroidered Racing Horses by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
Unit Price
per 
Island Canvas Short with Tequila, Salt & Lime in Dark Denim by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
Unit Price
per 
Embroidered Cisco Shorts Blue Seersucker with Martini Glasses by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
Unit Price
per 
Classic Fit Royal Oxford in Pink by Southern Tide
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
Unit Price
per 
Castle Harbor Stripe Sport Shirt in Coral Beach by Southern Tide
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
Unit Price
per 
The Gentleman's Spread Collar Sport Shirt in White by Southern Tide
Regular Price
$ 99.50
Sale Price
$ 99.50
Regular Price
Unit Price
per 
Sullivan's Solid Sport Shirt in Pink by Southern Tide
Regular Price
$ 99.50
Sale Price
$ 99.50
Regular Price
Unit Price
per 
Atlantic Plaid Sport Shirt in Royal Blue by Southern Tide
Regular Price
$ 99.50
Sale Price
$ 99.50
Regular Price
Unit Price
per 
Channel Marker Oxford Solid Sport Shirt by Southern Tide
Regular Price
$ 99.50
Sale Price
$ 99.50
Regular Price
Unit Price
per 
Beaufain Plaid Sport Shirt in Sunset by Southern Tide
Regular Price
$ 99.50
Sale Price
$ 99.50
Regular Price
Unit Price
per 
Cisco Short with Embroidered Hangover Special by Castaway Clothing
Regular Price
$ 98.00
Sale Price
$ 98.00
Regular Price
Unit Price
per 
Orange & Navy Oxford Stripe Suspenders/ Braces by High Cotton
Regular Price
$ 98.00
Sale Price
$ 98.00
Regular Price
Unit Price
per 
Save 48%
Isabel Grace Dress by Southern Tide
Regular Price
$ 97.95
Sale Price
$ 97.95
Regular Price
$ 188.00
Unit Price
per 
The Sea Breeze Linen Short by Country Club Prep
Regular Price
$ 95.00
Sale Price
$ 95.00
Regular Price
Unit Price
per 
The Broad Street Linen Short by Country Club Prep
Regular Price
$ 95.00
Sale Price
$ 95.00
Regular Price
Unit Price
per 
The Charlottesville Orange Pant by Country Club Prep
Regular Price
$ 95.00
Sale Price
$ 95.00
Regular Price
Unit Price
per 
Cisco Short in Red, White, and Blue Seersucker by Castaway Clothing
Regular Price
$ 89.50
Sale Price
$ 89.50
Regular Price
Unit Price
per 
Save 48%
Sadie Seersucker Embroidered Dress by Southern Tide
Regular Price
$ 82.95
Sale Price
$ 82.95
Regular Price
$ 158.00
Unit Price
per 
Save 48%
Seersucker Fit and Flare Dress by Vineyard Vines
Regular Price
$ 82.95
Sale Price
$ 82.95
Regular Price
$ 158.00
Unit Price
per 
South Carolina State Flag Needlepoint Flask in Blue by Smathers & Branson
Regular Price
$ 79.50
Sale Price
$ 79.50
Regular Price
$ 79.50
Unit Price
per 
The Merciful Marlin Resort Short by Country Club Prep
Regular Price
$ 79.50
Sale Price
$ 79.50
Regular Price
Unit Price
per 
Limited Edition Longshanks Needlepoint Flask in Blue by Smathers & Branson
Regular Price
$ 79.50
Sale Price
$ 79.50
Regular Price
$ 79.50
Unit Price
per 
Cisco Short in Royal & Navy Seersucker by Castaway Clothing
Regular Price
$ 78.00
Sale Price
$ 78.00
Regular Price
Unit Price
per 
Save 48%
Chase Long Sleeve Shirt by Castaway Clothing
Regular Price
$ 76.95
Sale Price
$ 76.95
Regular Price
$ 148.00
Unit Price
per 
Save 48%
Linen Pants in Stone by Country Club Prep
Regular Price
$ 75.95
Sale Price
$ 75.95
Regular Price
$ 145.00
Unit Price
per 

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!