Kentucky Derby 101: What To Wear, When to Wear It, and All About Hats!

by Cassie

After sending people to the Kentucky Derby for over 20 years, there is so much that my clients have taught me! So, as the weather warms up and we start to daydream about ice cold mint juleps, fancy fascinators, and Derby fashion, I wanted to share a little Kentucky Derby 101 for all of my friends who want to look the part on that special day at the track.

The History of Kentucky Derby Hats

Dating back to the famous Royal Ascot in 1711, it was ordered that guests in the Royal Enclosure follow a strict dress code including hats for women during the English horse races. When Col. Meriweather Lewis Clark traveled to the Grand Prix de Paris in 1872, he came back to America determined to establish a similar high-profile horse race. Clark and his wife enlisted the ladies of Louisville to attend the races to picnic with friends. According to Time Magazine, they knew part of creating the allure for the event would be positioning it as a fashion event so the dress code required “full morning dress” for men and women from the start. Today, patrons of the Kentucky Derby, taking place on the first Saturday in May each year, have been putting their fashion sense on parade since 1875.

What To Know Before You Go

There are a few simple rules to follow at the Derby:

  1. The most important characteristic of a Kentucky Derby hat is originality. Don’t be afraid to show off your personality with your hat!
  2. Let your hat be the star of the show by pairing it with a simple dress – and of course, make it sure matches. At HOM we always say, pick a dress to match your hat!
  3. If you are picking a hat before April 15th, I recommend finding your dress first. It helps narrow down your field of hat choices and makes deciding on a shape easier. We love it when people come in with 4 or 5 dresses as it gives us some latitude in what to wear it with. If you are coming in after April 15th, don’t panic. We still have lots of hats! However, there are way more dress options at that point than hats. Make life easier on yourself and pick a hat first, then find something to match.
  4. All of our hats come with boxes to make traveling easier. If it is under 22″, the box can be your airplane carry-on. Otherwise, you will need to check it with your luggage or ship it to your hotel in advance. I recommend mailing it priority 3-day, scheduled to arrive the Wednesday before so you have a few buffer days if something happens in transit.
  5.  Your hat should go down on the right, not the left, so nothing will be in your way as you watch the horses come around the track.
  6. Pick an outfit that you can wear all day and will pair well with a jacket, flats, and can handle rain. It’s not the time for flimsy fabric that might become inappropriate when wet.
  7. Again weather…it can be hot or humid or rainy or cold. Be prepared for any and all weather situations! Your outfit needs to be a bit of a chameleon.
  8. We see a lot of fascinators on Oaks Day and big hats on Derby Day. They can be packed in the same box and it gives you different looks for your photos. That being said, it is not hard a hard and fast rule. There are few occasions to wear these kinds of hats anymore (unless you are a British royal), so this is the chance to let your fantasies come out!
  9. Your hat style depends on your seats! In the seated area at Churchill Downs, known as Millionaires Row, you will see big brims and stylish fascinators. This is mostly because you don’t have to worry about rain or wind ruining your previous investment. These hats tend to be stylish and elegant, adorned with giant silk flowers, large bows, and beautiful ribbons. Whereas, in the infield, hats tend to be more eclectic and exotic. You will see more of a variety of shapes and sizes. Hats are not required in the Infield but trendsetters typically use hats to express their personalities here.
  10. There are rules on purse size BUT not hat size!

What is Oaks Day?

The Longines Kentucky Oaks is the race for 3-year-old fillies – female horses – held on the day before the Derby. The race was also established in 1875 and celebrates fashion and fundraising for critical women’s health issues. On Oaks Day you “pink out!” The historic race track is decorated in pink bunting and the more than 100,000 guests are asked to prominently incorporate pink into their attire in an effort to raise funds and drive national attention to the fight against breast and ovarian cancer. The event culminates in the Survivors Parade – a march of breast and ovarian cancer survivors that takes place on the racetrack.

Oaks Day Fashion

If you are planning to attend the Kentucky Oaks, you are encouraged to wear any color as long as it is PINK! From hats to handkerchiefs, suits to sundresses, sunglasses to stilettos! They even have the Oak Fashion Contest where you can show off your pink duds for an opportunity to win a Longines timepiece. Fashion is a key element of Oaks Day. It’s a day to get dressed in your finest, frilliest, most feminine attire and have a great time with the girls!

The HAT is the most traditional and important accessory on Oaks Day (headbands and fascinators are perfectly acceptable, too). So, start thinking now about your Kentucky Oaks ensemble – and extra points for wearing PINK!

Derby Tips

  1. Lather on the SPF – it’s nearly summertime in the Bluegrass State!
  2. Pick your horses the night before. You’ll want to head to the gambling line first thing!
  3. Ditch your heels! If you’re in the Infield, pack a pair of flats. Trust us.
  4. Practice: “Lou-a-vul” not “Lou-is-ville.” If you want to fit in with the locals.
  5. Don’t forget your bow tie, boys!
  6. Stop by the Brown Hotel for an Haute Brown. Arguably Kentucky’s most famous snack.
  7. Grab a piece of Derby Pie from Kern’s Kitchen.
  8. Enjoy a Mint Julep.
  9. Bring an umbrella with you to Kentucky. You can’t bring it inside the track, but if it is a gusher, you aren’t trying to buy one there with everyone else.
  10. If it is raining, carry your hats into the track in a plastic bag. Once inside, you can throw away the bag and don your topper.