Off to the Races: 2016 Horse Racing Season Guide

Off to the Races: 2016 Horse Racing Season Guide Kentucky Derby - Photo: iStockphoto/ Jill Lang

Ready, set, hats!

May marks the beginning of horse racing season, and its attendant mint juleps and mojitos, bright sundresses, and huge statement hats. To prepare you for high racing season, my team and I have put together a primer of the most important races, what’s at stake at each this season, and how to answer the most pressing question – what to wear?

Kick back with a mint julep and our guide to this season’s quintessential races.

Races to Watch

May 6 and 7, Kentucky Derby:

Held in Louisville, Kentucky on the first Saturday of May every year, the Kentucky Derby kicks off horse racing season. Held at the famous Churchill Downs, the competition is between three-year-old thoroughbreds, who battle it out on the racetrack for one and a quarter miles. The Kentucky Derby is the first of three key American horse racing events that, together with the Preakness Stakes and the Belmont Stakes comprise the “Triple Crown” of thoroughbred racing.

The race’s marquee social event is the star-studded, black tie Barnstable Brown Gala, held the night before the races every year in the jaw-dropping mansion of local social doyenne Patricia Barnstable Brown. It is one of the highlights of the Southern social scene, and a perfect occasion to break out your best Oscar, Carolina, or Miuccia. And once you’re at the races the next day, you’ll need a drink. If you’re feeling lucky with your bets, there’s no better way to toast to your luck than with Woodford Reserve’s $1,000 mint julep, which has been sold in a custom-designed commemorative cups at the Derby for the past ten years.

May 14, Iroquois Steeplechase: 

Hot on the Derby’s heels is the Iroquois Steeplechase, held near Nashville, Tennessee. Steeplechase has been held on the same course since 1941, and has been a fixture in Southern social calendars for just as long. The best views are from the “Tents in the Turn”– luxe, tented affairs with prime panoramas onto the track, and from the Skybox Suites, which are wood-paneled, climate controlled, and full of the crème de la crème of Southern society.

The hottest ticket in town is the Steeplechase-eve gala at the gorgeous and historic Belle Meade Planation. The soirée is invitation-only, but if you have a proper Southern belle on speed dial, you can bet she’ll have an in. You’ll have plenty of time to meet fellow race-goers in the preceding weeks, when all of Nashville congregates at the booming city’s best boutiques, including Reese Witherspoon’s new Draper James.

June 14 to 18, Royal Ascot:

For those looking to hop the pond for a mid-summer European escape, Royal Ascot is a must-go event on the British social calendar. Ascot is over 300 years old, and hats are required. The Royal Enclosure is the place to be, where Her Majesty Queen Elizabeth, along with the Duke and Duchess of Cambridge, watch the race each year. Race-goers imbibe over 50,000 bottles of champagne each year and nosh on 2,900 lobsters and 50,000 macaroons. Four hundred helicopters and 1,000 limousines ferry Ascot-goers to and from London and beyond.

What to Wear

Races have a very particular dress code, of course. For the ladies, statement hats or fascinators are the most essential piece of any outfit. While you could always head to Barney’s or Saks to find your perfect topper, some designers have taken to making extraordinary hats particularly for the occasion.

The Royal Ascot collection is designed in collaboration with eight of the United Kingdom’s most fabulous milliners, many of whom have been of service to the Royal Family. (We think the fascinator would be a particularly good choice to pair with your L.K. Bennetts, in a nod to the Duchess of Cambridge.)

Top American milliners include Maggie Mae Designs and Gina Conti. There are ostrich plumes and hand-pleated Parisian ribbon aplenty, custom orders are not uncommon, and the most important rule of all is that the same hat can never be worn twice.

As for the rest of your outfit, ladies should opt for a bright shift dress paired with Louboutin wedges and ropes of pearls– a classic, understated look that lets the hat shine! For gentlemen, a Brooks Brothers seersucker suit was practically made for Derby Day. Smarten up your suit with a bowtie, a pair of horse bit loafers (worn sockless, of course), and a fedora or bowler hat for a distinguished, dapper look.

And now, we’re off to the races!

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