Teach me how to Derby: 9 simple prep steps for a trip to Churchill Downs

There comes a time in every girls life when she must step from her lifelong comfort zone of New York City and brave the world beyond. In this case, that meant Louisville, Kentucky – home of Bourbon, horses, juleps, and their most notable combination: The Kentucky Derby.

Now, we New Yorkers come prepared for a lot of things. Most of us are unfazed by people talking to themselves on the street – or are those people talking to themselves are the street, and we can maneuver with relative ease around stalled 6 trains and still arrive on time – a true feat. But I had no idea where to begin when it came to prepping for the derby. And being the anxious packer that I am, I needed more than a few days planning and at least a few consulting phone calls with friends in the days leading up to the big event. But while this newbie fretted and over-shopped at Saks, Shaye Swanson kept cool and carried on her family tradition of attendance. For her veteran derby approach, check it out here. But if you want some newbie tips on Derby Survival 101, you are in the right place. Hold on to your fascinators, we’re about to get Derby.

1. Go big or go home. Seriously. This is a once in a lifetime opportunity (unless you’re lucky enough to be a Louisville native) so you best make the most of it. That means the works – hot dress, sick shoes, and of course a hat – or fascinator, as the case may be. My dress for the Oaks was an easy find that reaped tons of compliments from strangers and minor celebs alike thanks to Kirribilla. The colors were perfect for spring, while the peplum waist made it fashionably current. And on Derby Day I sported a white, lace Tibi with a deep-V back.  I then opted for a fascinator from LaCrasia in NYC and from the moment I put it on I thought two things: First, when’s the next royal wedding? Second, I am wearing a teacup on my head. At the end of the day, it was perfect and I fit right in.

Fair warning readers, you’re going to feel like an idiot trotting this thing around town on your head until you get to the actual races. But hats and fascinators are part of the ticket here. Once you reach Churchill Downs, I can promise that even the most intense hat you can find will be nothing compared to the women who look like birds nested, then blew up, on their heads. It is fantastically awesome while also slightly petrifying, but you’ll be mad at yourself if you don’t at least try to blend in.

2. Comfortable shoes. Once when I was eight, my hairdresser yanked too hard on my hair and I, of course, said “ouch.” I was then given a pearl of wisdom I’ve carried with me ever since: “Beauty is pain, kid.” In most cases, I ascribe to this philosophy. For example, you don’t buy Louboutins because they’re so comfortable you want to run a marathon in them. But for the derby, I’m going to have to say tread carefully when choosing your shoes. Caveat: If you’re going to be in the infield, definitely opt for a flat or wedge – there’s nothing worse than the grass sucking at your heels with every step.

My lesson of the weekend was that, contrary to Fran’s wisdom, beauty, style, and comfort can live in the same place. And I hereby solemnly swear that after two straight days of standing, schmoozing, and sitting in my electric turquoise Jimmy Choos, I’ll be hard pressed to buy another pair from anywhere else. My bank account thanks me. But an alternative is to pack flats. This is actually a good tip for life in general, but if you know you’re going to be on your feet for extended periods of time in heels, bring flats. I got a great pair of foldables that fit perfectly in most of my purses – including the mini-cross body ones I used to love bringing to college formals and mixers! I popped my snake print folding flats into my bright pink Rebecca Minkoff for the Derby and had no problem keeping up with the speed walkers I was with as we tried to ditch out quickly in order to avoid traffic. Allow me to say publicly that my hosts were fantastic drivers in high-stress situations. True “presence of greatness” skills.

3. Bring a poncho. My mom really saved the day on this one because before I left she slipped a pack of 5 plastic ponchos into my suitcase. When it poured on Derby day, we were elated to have them – especially because umbrellas are not allowed. So take a page from my mom’s playbook and pack some ponchos.

4. Place your bets. I’m not one to advocate for bad habits, but hey, when in Rome. The Derby is tons more fun if you can cheer on a horse that has your money actually riding on it. After countless attempts at calm explanation, I think Alex gave up on teaching me how to bet. And I simply gave him $20 to put down for me and wished him luck on his way to the betting booth.

A tip: Make friends with the guys who buy the programs and write notes in the margins. They’re like the straight-A students at the front of the class, and you definitely want to their advice. In fact, Shaye had more than a few tips for me before the big race. Not that I listened. Despite my luck-wishing, I came out of the weekend with a big 0 in the win column.

5. Put down the Mint Juleps. Gasp! I know, I know, they’re the drink of the Derby. But for any of you who have been to NOLA, I liken Mint Juleps at the Derby to Hurricanes and Hand Grenades on Bourbon Street – they’re great novelty drinks and then the sugar hangover hits. Not good. But since Kentucky is known for it’s Bourbon, I went that route. Cheers to still feeling touristy, with a splash of Ginger Ale!

6. Read up on U of L. This tip was given to me by the person who invited me: “No matter what, tell people you’re a Louisville fan. Oh, and you were really excited about the National Championship.” Now, I’m not sports-inept. I knew that Louisville basketball had a sick trip to the finals – complete with grotesque and highly publicized injuries – and an even sweeter victory. But Alex’s advice turned out to be pretty good. On at least a handful of occasions someone asked me what I thought about UL, and I got to respond like an aware out of towner who supported the local team. Hey, I take street cred where I can get it. It didn’t hurt that Louisville Coach Rick Pitino was working the Derby crowd as well.

7. Take a look at the lyrics to “My Old Kentucky Home.” I was told early on that this was the best part of the Derby. And despite the teleprompter gods’ mistakes with the lyrics scroll on the JumboTron, it quickly became clear why. This is the equivalent of hearing Sinatra at a Yankees game during a particularly important playoff run. It’s tradition. “You’ll cry,” Alex’s mom told me. She didn’t realize that she was talking to someone who cries at everything from tacky Gossip Girl endings to s. The song is a great moment. Practice your singing for next year here.

8. “Instagram it.” Take pictures – be it with your friends, (awkwardly) by yourself, the classic steeples, or the C and D-list celebs and athletes that often wander their way into this event every year – and post them everywhere, shamelessly. My favorite photo was taken with N*Sync’s Joey Fatone — proving once and for all that tween dreams really do come true and you’re never too old to geek out over your favorite boy band has-been. Check out my pictures in the gallery above!

9. It’s a marathon, not a sprint. I will recycle this old college, Mardi Gras adage and say that it applies just as much then as it does to the Derby. It’s a full weekend of events so have fun (duh) but pace yourself.

A big shout out to my hosts in Louisville for making Derby weekend 2013 absolutely unforgettable. And to all of you Derby go-ers, newbies or vets, happy betting, drinking, and Derbying!

Read more about a veteran’s approach to the Kentucky Derby — and all of the events that lead up to it — here.

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