When it comes to formal headwear, we suspect the unfortunate contraption donned by Princess Beatrice at The Royal Wedding last year* may be the common image singed into the minds of the masses. Despite this royal fashion fail, there is a different kind of royal hat-wearing occasion that goes down every spring on American soil—The Kentucky Derby. In the spirit of this marvelous May menagerie, here is a brief history of derby fashion amid do’s and don’ts to dress for the Run for the Roses.

In 1872, Col. M. Lewis Clark, Jr., grandson to The William Clark, of the Lewis and Clark expedition, spent time in England and France where he was educated in all things luxury, horses and racing by a group of racing enthusiasts. Inspired by his experiences at the Epsom Derby and the Grand Prix de Paris, Clark returned to Kentucky and promptly organized the Louisville Jockey Club.

Having a taste for European luxury, Col. Clark naturally brought a passion for fashion back to the Bluegrass State. In the early 1900s, Churchhill Downs was the closest thing to a red carpet; thus, the local felines embraced their opportunity to be seen in the latest fashions, and made history while doing so. A journalist from the 1901 Courier Journal famously stated, “The seats in the grandstand were filled with gaily dressed women and men. The mass of green, pink, red, yellow, blue, and all the colors of the rainbow, blending into one harmonious whole was as beautiful a sight as His Eminence in the lead.”

Fashion history has had a love affair with the patrons and pageantry of Millionaire’s Row, the premier seating for the fortunate few who get to watch the races from the sixth or fourth floors of the stadium. Guests are indulged with table seating, a balcony view of the track, first rate cuisine, full bar and of course, televisions that play the races. Bennett Spector, senior writer for The Bleacher Report calls it “Gone With the Wind meets The Real Housewives,” the dress code being nothing short of immaculate.

If you were to Google phrases such as “seersucker,” “silk,” “four-inch heels,” “oversized handbag,” “fedora,” “fascinator,” you’d be on the right track for finding your derby duds.

Here are a few additional tips to inspire your war for the roses wardrobe:

  1. If your hat is going to be the life of the party, keep your dress simple. This does not mean you have to stay away from patterns, but your frock should be feminine and well cut—think The Duchess (Kate, not Fergie).
  2. If your hat design is simple, it’s not a bad idea to stay in the classic mode by keeping the dress or suit simple yet elegant as well. “Dress shabbily, they notice the dress. Dress impeccably, they notice the woman,” said one Coco Chanel.
  3. If you have long hair, showcase a sleek pony slightly askew, so it flips over your shoulder and sits well beneath your hat.
  4. Keep your jewels simple. Don’t let your ears steal the show from your fascinator.
  5. Gloss those lips! The hat will frame the face and likely dip below the eyes, keeping them mysterious. Your pretty pout will be the focal point beyond the hat.

Cheryl Says

In an effort to keep your focus on the horses and not a raging headache, make certain your hat is the right size. You should be able to fit a couple of fingers between the brim and your head. Nothing is more nagging than an uncomfortable pair of shoes or a hat that’s too snug!

*Please note that while we do not approve of the fascinator worn by Princess Beatrice at the 2011 nuptials of William and Kate, we do commend her bravery. It should also be noted that, given the opportunity, we would not pause before knocking an innocent old lady out of the way for the opportunity to try on said fascinator and snag a few photos for our Facebook profiles.