Style

Local Plunder

The Right Clothes for Derby Day

One week from Saturday, you might be headed to the Gold Cup. Or you might ensconce yourself at a downtown hotel bar to take in the Derby. Either way, horses will be involved. (Also: bourbon.) And you’ll want to look the part. No, not like a jockey. With this stuff...

FOR YOUR HEAD

A Hat That Proves You’re a Good Guy

What: A hat that can only be worn on two occasions: when you’re watching the ponies, or when you’re overseeing your rum operation.
Why: You’re going to need to keep the sun out of your eyes. To say nothing of the glint from all that coin you’re going to make on your exacta.

FOR YOUR NECK

Jockey-Inspired Ties at Vineyard Vines

What: From VV’s Kentucky Derby collection, this bit of neck silk is based on patterns from actual jockey silks.
Why: Because even as you’re hacking up bunches of mint and furiously shaving ice, you’ve got to keep things civilized. And it’s easier than starving yourself to fit into an actual set of silks.

FOR YOUR TORSO

A Blazer with Some Tradition Behind It

What: A nice, bold blazer, inspired by the Cambridge University rugby team’s trip to America in 1934. And English dandies everywhere.
Why: You want to stand out from the crowd as you try to talk people into your idea of playing rugby on horses.

FOR YOUR LEGS

Derby-ish Jeans from Shipley & Halmos

What: A bit of slim-fit denim, in the oh-so-traditional color of “clay mauve.” Also known as “dark pink.”
Why: They’re just the unholy mashup of hipster and prepster that will keep them guessing. Plus, they match your victory cigar.

FOR YOUR FEET

Seersucker Sneakers at Brooks Brothers

What: Slip-on Keds, now in breathable, senatorial seersucker.
Why: You’d like to be fleet of foot should you decide to race the horses around the infield. Or should your bookie decide not to pay you.