Pony Up

A Pictorial Analysis of Your Derby Gear

The odds of We Miss Artie winning the 140th running of the Kentucky Derby: 50:1. The odds of you winning the Lifetime Seersucker Achievement Award at tomorrow’s Kentucky Derby party: 1:1... assuming you take note of our advice below.

UD - A Straw Boater Fit for the Races

A Straw Boater Fit for the Races

Tomorrow’s forecast at Churchill Downs: boater weather. Enter this American-made straw number with a sweat-wicking ribbon around the crown. What’s sweat if not something to be wicked by a ribbon...
Post-Derby Applications: Schooner parties. Midsummer ball games. Running for mayor of Hattiesburg, Mississippi.

UD - For a Categorically Perfect Mint Julep

For a Categorically Perfect Mint Julep

It’s solid pewter. It’s engraved with your initials and the initials of the current governor of Kentucky. It’s... basically what Indiana Jones was after in The Last Crusade. Assuming he was after a mint julep cup.
Post-Derby Applications: For drinking more juleps, obviously. Or wearing as a miniature pewter fez, less obviously.

UD - Because Seersucker Is Mandatory

Because Seersucker Is Mandatory

There’s seersucker, and then there’s seersucker made by the 105-year-old, New Orleans–based haberdashery that more or less made it a thing. Guess what kind this jacket is.
Post-Derby Applications: Weekend strolls. Country club happy hours. Quitting your day job and hitting the road with a barbershop quartet.

UD - A Tiny Pair of Horses for Your Wrists

A Tiny Pair of Horses for Your Wrists

Now, cufflinks aren’t mandatory at the Derby. But there’s something to be said for a set of 18-karat gold ones with racing horse heads reverse-painted on them. That something being, “Hey, nice cufflinks.”
Post-Derby Applications: Golf ball markers. A Mother’s Day gift, if you’re terrible at gifts.

UD - The Only Reasonable Derby Footwear

The Only Reasonable Derby Footwear

Oh, right, you’ll need shoes. Something light, but something bold. Something like these two-tone leather brogues made by one of England’s most legendary cobblers. Or so the cobbling legend goes.
Post-Derby Applications: Cricket matches. Elvis impersonations. “Just wearing them.”

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