May 23, 2016

A Beginner's Guide to the Kentucky Derby

Everything you need to know about the Kentucky Derby.

A Beginner’s Guide to the Kentucky Derby

The 2016 Kentucky Derby was two weeks ago, but we are still in the midst of the Triple Crown season. Plus, it’s never too early to start planning ahead for this bucket list event. So, we have a special treat for you today… We are answering all the questions you’ve ever had about the Kentucky Derby! Consider this a beginner’s guide to the Kentucky Derby with answers to your seven most pressing Derby-related questions.

1. Why should I attend the Kentucky Derby?

First things first: why should you even care about the Kentucky Derby (“the Derby”)? Well, obviously, if you are a fan of the sport, you will be drawn to the event. But even if you don’t know much about horse racing, you should consider attending the Kentucky Derby because it is such an important part of Americana. While it may be known as the “most exciting two minutes in sports” for its approximate duration, the Derby is so much more than those two minutes.

America’s best-known race is the most highly attended sporting event largely because of all the traditions and festivities that place off the track. It’s so much more than a “just” a horse race. Not only is the horse racing top notch, but the people watching can’t be beat. It’s two straight days of non-stop racing action, people watching, fashion fun, and parties around the clock!

2. Tell me all about the race itself.

The Kentucky Derby is held on the first Saturday of May in Louisville, Kentucky, at Churchill Downs. This year marked the 142nd running of the race. On May 7, 2016, a total of 167,227 people attended the race. That’s just slightly under the high-water mark set last year at 170,315 people.

The Derby race is 1.25 miles in length (2 km). Only three-year-old thoroughbred are eligible to run in the Derby. The Kentucky Derby marks the first leg of what’s commonly referred to as the Triple Crown of thoroughbred horse racing.

The Triple Crown consists of the following three races:

1. The Kentucky Derby at Churchill Downs in Louisville, Kentucky

2. The Preakness Stakes at Pimlico Race Course in Baltimore, Maryland

3. The Belmont Stakes at Belmont Park, just east of New York City

Each of the races is run on a dirt track, though the length of each race differs, as does the location. Also, the races are held on a very tight timetable, with the Preakness taking place two weeks after the Derby and the Belmont taking place three weeks after the Preakness.

All of this makes the Triple Crown extremely difficult to achieve. This year, Nyquist won the Kentucky Derby, but this weekend he fell to Exaggerator in the Preakness Stakes. So there will be no Triple Crown this year. You might remember that American Pharoah won the Triple Crown last year. Prior to that, it had been 37 years since a horse had won the crown! Only twelve horses have ever achieved the Triple Crown level of greatness.

3. How does a horse qualify for the Kentucky Derby?

As mentioned above, horses are eligible to run in the Derby only once: the year in which they turn three years old. The road to the Kentucky Derby includes a series of 35 preparation races. In those 35 races, horses can accumulate Derby points.

At the end of that series of races, the twenty horses who have accumulated the most points on the road to the Derby are the ones who are offered a spot in the twenty-horse field of the Kentucky Derby. If a horse has to withdraw or its team chooses not to run it in the Derby, the next four horses in the standings are eligible to enter the race, in order of their points standing.

In the end, at most, twenty horses will compete in the Kentucky Derby. Only those horses running in the Kentucky Derby will have a chance to win the Triple Crown. Remember, though, that a horse does not have to run in the Kentucky Derby in order to enter the Preakness or Belmont.

4. Can you explain how to bet on the races?

I certainly am no betting expert, but I can share the basics ideas and terms of betting on the races.

Betting odds are calculated based on the amount bet on a horse in comparison to how much is bet on the other horses in the field. The more money bet on a single horse, the worse his odds will get. The odds continually change over time until the betting window closes at the post time (or, start time) of the race. So, that means you don’t really know the exact odds of your wager until the race starts. Proceeds are paid out based on the final odds at race time.

Here are some of the simplest, most straightforward bets:

-If you place a “win” bet, that means the horse must win the race in order for you to win the bet.

-If you place a “place” bet, that means the horse must finish first or second for you to win the bet.

-If you place a “show” bet, that means the horse must finish first, second, or third for you to win the bet.

5. What traditions do I need to be aware of?

Hats, hats, and more hats : The first and most important probably goes without saying, if you just glanced at these photos. That’s right: hats are pretty much a requirement for the Derby. The pageantry of the event is all part of the fun. When it comes to Derby headwear, go big or go home! While styles vary from elegant to extreme, one trait that almost all the hats have in common is that they are oversized. Play up that southern charm with a big hat.

Cocktails: Even if you’ve never been to the Derby, you are probably familiar with the mint julep. The mint julep is the cocktail that everyone associates with the Derby. For over 100 years, the drink has been made with fresh mint and Kentucky whiskey, and it is served in a silver cup. It is estimated that almost 150,000 mint juleps were served on Kentucky Derby day!

What you might not know, though, is that there is another cocktail tradition. Though this tradition is only ten years old, it has caught on quickly! Served during Friday’s Kentucky Oaks races (the day prior to Derby day), the Oaks Lily is a sweet combination of cranberry juice, vodka, triple sec, and some sweet and sour mix. It’s pink color goes well with the pink theme of Friday’s races.

My Old Kentucky Home: Since 1936, this anti-slavery ballad originally penned by Stephen Foster in 1852 has been performed by the University of Louisville Marching Band as the horses make their way from the paddock to the starting gate. The moment the horses step on the track, the music begins, and everyone sings along in unison is quite a moving moment.

Roses: They call it the “run for the roses” for a reason. Since 1896, the winning horse has been awarded with a beautiful garland of red roses, making red roses practically synonymous with the Derby itself. Each year, a garland of more than 400 red roses is sewn into a green satin backing with the seal of the Commonwealth on one end and the Twin Spires and number of the race’s current running on the other hand. If you make it to the Derby, try to sneak a peek of this beautiful creation. It’s usually on display near the paddock prior to the main race. It really is a site to behold.

6. What should I wear to the Kentucky Derby?

The Kentucky Derby is a wonderful opportunity for a woman to express her own take on a genteel Southern belle. There are no set-in-stone, hard and fast rules. These days, Kentucky Derby outfits run the gambit from casual sundresses to cocktail dresses and even more formal. Your outfit choice is somewhat dictated by where you plan to spend the day. In the reserved seating areas (particularly the suites), dressing will be a little more upscale than it is in general admission or infield area. .

What you might not have realized about the Derby is that it is actually a two-day event, meaning you’ll need not one, but two outfits! That’s right: two hats and two dresses.

As alluded to above, Friday is Kentucky Oaks day. This is a full day of the fillies (female horses) racing. In the spirit of it being ladies day at Churchill Downs, the track partners with a charity to raise money for the education, support, and empowerment of young women nationwide in prevention of breast and ovarian cancer. The race track itself and all the attendees tend to deck themselves out in pink on Friday, creating a beautiful sea of pink everywhere you look!

Then, of course, Saturday is Derby day. Attendees often gravitate towards looks with floral prints or the color red to tie into the red roses theme of the day.

You might ask: which comes first? The dress or the hat? That’s a great question… I go both ways on this.

For instance, for Kentucky Oaks day this year, I knew I wanted to wear this stunning Philip Treacy hat in the requisite color of the day, pink. When I spotted this gorgeous pink and navy Sachin & Babi dress, I knew I had nailed down the essentials of my outfit.

However, for Derby day, I took a different approach. As part of Donegal Racing, our team colors are yellow and green. Furthermore, my dear friend Donae from The Vintage Contessa who attended the Derby with me this year offered to let me borrow this fabulous Hermes 35 cm Birkin bag in yellow and green — perfect for Donegal Racing! So, with the color palette and bag chosen, I selected this elegant Tibi open-back floral dress. And then finally, milliner Eugenia Kim custom designed this hat to go with my look for the day. I loved seeing the talented Eugenia Kim’s modern, minimal, chic take on a Derby hat!

7. What else do I need to know?

1. Plan early : If you’re only going to do the Derby once, make sure you do it right! Start planning now.

2. Rest up : you’ll need the energy!

3. Live it up! Once you decide to go, embrace the weekend all you can. Immerse yourself in the experience. There’s nothing else like it.

I’ve attended the Derby over the last five years. Hopefully, these insights I’ve gained are helpful to you. If you have any further questions, just let me know! I’m happy to answer.

Have you ever been to the Kentucky Derby? Have you been to any horse racing event? Whether you attend the Derby in person or participate in a party, embrace the traditions of it all and have fun with it!

To learn more about the fashion and social side of horse racing, be sure to visit our friend Bri at Fashion at The Races.

Special thanks to Joe Lyman Photography for all the photos!

Kentucky Oaks look : Sachin & Babi Calla dress (c/o) (gown version here; also love this dress on sale) | Philip Treacy hat | Manolo Blahnik white pumps | Chanel bag from The Vintage Contessa (less expensive similar option here) | Karen Walker sunglasses | Dior rouge lipstick | OPI gelato on my mind nail polish

Kentucky Derby look : Tibi Bella floral open back dress (also here and here) | Eugenia Kim custom hat (c/o) | Hermes Birkin bag from The Vintage Contessa | Jimmy Choo sandals (older; similar here) | Karen Walker sunglasses | Nars heat wave lipstick | OPI gelato on my mind nail polish


  1. Ellen says:

    This is by far the most helpful Derby guide I’ve found yet, thanks so much for posting! My husband and I are planning on attending the 2019 Derby & I’ve found two different ‘Derby Eve’ parties, I was curious if you suggest one over the other? One is called Fillies and Lillies and is held at the Kentucky Derby Museum the other is called Fillies and Stallions and is held at the Mellwood Arts Center. So, which is the one to attend? Thanks!

    1. Oh I’m so glad to hear, Ellen!

      Actually, I have to say that without a doubt, for Derby Eve, I recommend the Barnstable Brown party! I’m not exaggerating – it is really my favorite party ever! If you enjoy music, you won’t want to miss it. So many musical stars and legends singing and performing while you’re up close and personal.

      It’s a charming, special party.

      Let me know if I can help any further!

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