What to Wear for Derby Day

by Scott Wagner

Fedoras are fair game

The Derby Stakes in England and the Grand Prix de Paris in France inspired Col. Merriweather Lewis Clark Jr., to start a similar kind of race outside his hometown of Louisville in 1875. 

Cut to the Kentucky Derby

Around this time, there were a number of well established horse races throughout Europe, but in the U.S., racing was seen as a bit seedier—a gambler’s sport—making it less of a social affair. To fix this problem, and to draw a different kind of crowd, Clark insisted that morning dress be worn (think tails and ties) to his Kentucky affair. People did, in fact, show up to place bets in their best. 

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Today, you’re not required to wear morning dress to the race, but it’s no less a fashionable affair. Fascinators, fedoras, suits, and ties are all fair game. And, of course, there’s the other thing the race has a long history with: great bourbon. A key part of the Mint Julep, the official drink of the Kentucky Derby since the ’30s, it’s the only other thing you need (aside from a good suit) on the first Saturday in May. 

Kentucky Derby Suits 

A good suit is where it all starts. Think of it as your base, upon which you will layer many more excellent things. 

J. Crew Ludlow Suit, $228, available at jcrew.com

Even straight off the rack, the J. Crew ludlow has a cut that looks good on just about everyone. Go with this and you can pretty much count on skipping a trip to the tailor. 

Light Brown Havana Suit, $899, available at suitsupply.com 

Navy blue not your thing? Go for light brown in a warm weather fabric. And make it a three piece if you’re looking to really stand out from the crowd. 

Navy and White Stripe Travel Suit, $2,495, available at paulstuart.com 

Don’t be put off by pin stripes. They’re seriously slimming and perfect for a day at the races, but not an afternoon at the track. 

Kentucky Derby Fedoras 

The queen has a crown, but you’ve got a fedora. They’re worth it for two reasons: they protect your face from the sun and, rumor has it, they bring good luck. 

Rothney Fedora, $115, available at baileyhats.com

Hunter S. Thompson wore one and so can you. 

Stratoliner Fedora, $93, available at stetson.com

Wear it on Derby Day, Mother’s Day, and the Fourth of July. These hats can be worn for anything so long as there’s sun. 

$89.50, available at vineyardvines.com 

A darker shade of beige like this goes well with suits in lighter hues and the contrasting band dresses it up a bit. 

Kentucky Derby Accessories 

No Derby look is complete without a good pocket square and tie to match. 

Back Stretch Pocket Square, $40, available at efmeeks.com 

Some say the Back Stretch is where the winning horse makes itself known. Why not pay tribute to such sacred land with your pocket square? 

Bowtie, $65, available at efmeeks.com 

Be bold and tie on a bowtie like the gents at the original derby. 

Necktie, $125, available at efmeeks.com

 A Necktie with jockey vibes is more than fitting. 

Editor’s Note: Top photo by Jeff Griffith on Unsplash.

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