1. Dressing to the nines is a must. Here, our travel companions Heather and Jake show how it’s done. Jake served in Afghanistan with my Jake. Don’t Heather and Jake look grand?
Jake’s suit was tailor made in Kabul, Afghanistan, just for this occasion.
Who knew Kabul had its own Savile Row?
His was probably the only carefully crafted handmade suit at the Kentucky Derby that cost $95! Looking good, Jake!
My Jake looked good too, though I wish we would have spent more time “crafting” our outfits.
As it was, I wore an old dress from American Apparel, an old straw hat that I pinned with a giant fake flower from this amazing store in nearby Bardstown called Peacock on Third (I couldn’t find an actual website for the store). Which leads me to my second point:
2. Don’t bother buying a hat before you arrive in Kentucky.
I mean, you can, but it’s not imperative. Unless you live in a loud and proud fashion city like Atlanta, Los Angeles or Houston, fabulously flamboyant hats that don’t break the bank are hard to come by. Luckily, the state of Kentucky is chock full of ‘em and lots of cool hat accessories by Derby Day. My pink flower from Peacock on Third only cost $19!
3. Forget high heels
Churchill Downs is very big and very crowded so unless you’re a VIP lucky enough to be whisked to the front of every line in your limo, expect to do some serious walking. Heather began the day in these very pretty, ladylike flats (read, blister makers)…
…and ended the day in a pair of anti-chic flip flops decorated with whales that Jake had to buy for FIFTY DOLLARS at the Derby to save his beloved’s battered feet!
4. You have to wear a hat
Ladies, don’t even think about showing up to the Derby without a crown. Guys too! Your naked head will embarrass you. Derby Day is not a time for fashion timidity. Go big or go home.
5. The natty Great Gatsby 1920s hipster trend lends itself very nicely to gentleman’s Derby attire.
I can’t tell you how many beards, rumpled old hats, bow ties, suspenders, even knickers I spotted on gents at Churchill Downs. I almost felt like I was at a speakeasy in Bushwick! It was very refreshing to see grown men dress.
6. Dropping hundreds of dollars on primo tickets doesn’t necessarily mean a primo experience
Jake and Heather splurged on Grandstand seats, which aren’t cheap. Jake and I, meanwhile, slummed it with the much cheaper in-field tickets, $50 each. Grandstand tickets meant Jake and Heather had a seat, but there was no shade (it was 86 degrees that day) and they still had to wait in the same long lines as the rest of us….lines for food, for mint juleps, for placing bets….and don’t even get me started on the line to the ladies room!
In-field tickets are okay if you’re willing to show up very early — like, four o’clock in the morning! — and stake out a spot on the perimeter offering a view of the track, bringing with you a tent, chairs and a cooler stocked with food and drinks. Otherwise, the track is invisible from the in-field! You can’t see a thing! THere is nowhere to sit down! And there’s a very strong Spring Break atmosphere in the in-field so Jake and I spent a good part of the afternoon trying not to get barfed on.
7. Don’t rely on your cell phone
I made the mistake of leaving Jake in the betting line while I went to get us a round of mint juleps. I ended up standing on line forever. When I tried to call Jake to tell him where I was, I couldn’t get a signal. Systems were jammed. Jake couldn’t find me. We ended up separated in the in-field for a good hour, me pushing my way past a crowd of college boys shouting to an obliging Jenna Jameson wannabe, “Show us your t*ts! Show us your t*ts!”
8. It’s a once in a life time experience
Meaning, I’m not sure I’ll go back to the Derby next year. Don’t get me wrong, I had a great time. It was so much fun dressing up, mastering mint juleps, holding hands with Jake around Churchill Downs (after we found each other, that is), checking out the shenanigans of those wacky young people, but I think my days of standing around elbow to elbow in a crowd of drunk people are over. However, if I hit the lottery and can afford my own box seats in the shade with a waiter, I am there.
9. Oh yeah, I didn’t win.
No box seats for me next year.
{ 6 comments… read them below or add one }
Thanks for an excellent report. I lived in Louisville for 12 years. I went to the Derby once – in the infield. That was 1991 and it sounds like the same people are still there! You are correct – I had an excellent time, very glad I went and I would never go again unless it was to a sky box with a butler and maid.
Love the suit and hat of your friend, Jake. Very sharp. Very dapper.
Each of you looked nice in your own way. The flower really made your hat. Some of the hats I saw on TV were nothing but statements to see who could be the most ridiculous. Thanks for telling what it was really like. I don’t feel bad about only seeing it on TV.
Like Megan, I live where there are a lot of large events, but we go to them less and less. There comes a time when the hassle isn’t worth it.
When we lived in Kentucky we went to the Derby for eight years straight and saw a horse running in a race ONCE. But we had a great time. If you want dress up racing with out the craziness, check out Keeneland in October.
I went in 2007, and had grandstand seats. Lovely time (a dream since I was a little girl in WA), but it was hot & humid. And overcast. I made a point to watch the races. The Derby itself was more difficult as everyone stands. I’m not tall and there are big hats. C’mon ladies! I do want to go again, this time to check out the rest of Churchill Downs on Derby day.
John D, thanks for the advice!
Loved this post! I would like to go the the Kentucky Derby one day! It is such a unique tradition!