Kentucky Derby 2013: A rain-filled weekend recap

I’ve been pretty lucky to continue a family Derby tradition that goes back to the 1950’s. I simply can’t resist the pomp and circumstance, fashion, mint juleps, and horses. I guess all this makes me a Derby veteran, of sorts.

Although the Derby itself gets the most hype, the two weeks leading up to the first Saturday in May are full of things to do. Whether you decide on a grand ball, distillery tour, or a chance to hold Mickey Mantle’s bat at the Louisville Slugger Museum (the two latter are boyfriend approved), you’re bound to have a marvelous time in the whirlwind leading up to Derby.

Here are some highlights from my experience attending the most exciting 2 minutes in sports!


Thursday: Taste of Derby

(What I wore: Dress by Naven, shoes by LK Bennett, bag by Rebecca Minkoff, and jewelry by J. Crew and Stella & Dot)

Who can resist a red carpet event? I definitely can’t. The 4th annual Taste of Derby was the perfect combination of fine food and fashion for a cause. As soon as I walked in the door, an attendant handed me a beautifully branded wine glass and directed me toward booths of renowned chefs from all around the country. I was happy to see that women were already taking an opportunity to wear crazy fascinators. I loved trying the limited edition peach mint juleps from Woodford Reserve, and even got a personalized Stella Artois Derby chalice.

*Tip: Bring a larger handbag for the oversized party favors. Embrace your inner kleptomaniac.


Friday: The 139th Kentucky Oaks

(What I wore: Dress by Diane von Furstenberg, hat by Emma B, shoes by Michael Kors, bag by Rebecca Minkoff, and necklace by Stella & Dot)

Oaks Day is all about ladies, fillies, and lilies. The crowds aren’t as overwhelming, and for the first-timers it is an excellent time to figure out Churchill Downs. Until you experience it, you will never understand the logistical mess that is Churchill Downs on Derby weekend.

This year, all of the well-dressed ladies I spoke to (in lines, as most of the weekend is spent standing in food / betting / restroom / ATM / bar lines) decided to switch their Oaks and Derby day outfits due to the imminent downpour. There was no way I’d wear a white DVF in rain.

The best news for all of you non-bourbon lovers out there is that Oaks day has a signature pink drink called the “Lily,” which is kind of a cross between a vodka cranberry and a Cosmo. And just as you’re about to be overwhelmed by the pink of it all, remember that this year it was all about honoring breast cancer. Between all the Lilly, Milly, and Lily cocktails, Oaks day was a celebration of pink, preppy, and fabulous.

*Tip: Take mental notes of the shortest lines you were in, and the shortest routes you navigated around Churchill Downs. You’ll thank me come Derby Day.


Saturday: The 139th Kentucky Derby

(What I wore: Dress by Diane von Furstenberg, fascinator by Nigel Rayment, bag by Rebecca Minkoff)

Oh, Derby. I think I stalked the forecast at least 10 times a day, and I simply had to accept that the weather would be terrible. My family’s box wasn’t undercover, so I made the game time decision to switch from delicate Stuart Weitzmans to my beloved cowboy boots, fight the rain-induced frizz with a last-minute up-do, and accessorize my blinged out DVF dress with a raincoat and poncho. It was quite a spectacle watching the fashion shift from chic dress and hat combos to cutest poncho and improvised rain gear ensembles. A definite highlight was getting to see the ladies cover their hats with trash bags a la 90s grunge so they wouldn’t be ruined.

This was arguably the most social Derby ever, as 150,000 people had to squeeze together to stay dry. In my section, I was invited into a new box and got to avoid the rain – which was totally worth sharing my kettle corn. But rain or otherwise, Derby Day is truly all about fast 3-year-old horses that don’t even know that this is the biggest moment of their lives. And with years of betting under my belt, I had more than a few tips on where to place your money. When I met with Ali, I told her that I really liked Mylute and Revolutionary. Those horses actually did really well (3rd and 5th), but I still went home a loser… unless I count seeing Joey Fatone on the red carpet. That was awesome.

*Tip: The safest bet is to bet a horse to show (3rd place)… or not bet at all. But where’s the fun in that?

Read more about Derby Weekend 2013 from a newbie’s perspective – 9 “How To Derby” tips included!


bettingderbyDVFhorseskentucky derbylouisvilleoaks
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