In 2004, I attended my first Kentucky Derby. I was 20 years old at the time, and my grandma, being the clothing-obsessed gal that she was, decided that I just couldn’t walk into Churchill Downs on that super special day without a proper topper. We drove to Louisville one weekend and hit up all of the department stores looking for the one. Finally, after lunch, we stopped in a seasonal hat shop, where I spotted a vintage Kokin. Black, wide-brimmed, and drowning in black coque feathers. It’s crown was covered in a black fishnet, with a black pearl at each intersection. It was gaudy, and beautiful, and perfect.
I have no idea how old this thing was, and I can’t imagine the original price tag, but I do remember that the dollar amount on the tag scared the daylights out of me. I remember Mamaw bartering with the shop’s owner, and before I could see the check she had written, it had exchanged hands, and I was given a hatbox full of beauty that I never dreamed I was worthy of.
My first Derby, I wore my ridiculously ostentatious hat with a strapless white dress. I didn’t place a single bet, but Smarty Jones crossed the finish line, and my boyfriend-at-the-time and I screamed and cheered as if we had thousands of dollars riding on the whole thing.
Three years later, in February, we lost my grandma. I was still trying to heal when Derby 2007 rolled around. B and I had been dating for just over a year at that point, and he suggested that in order to feel a little closer to her that day, I should break out the “big black hat” as it was known at the time. We threw down $2 on a trifecta of Street Sense, Hard Spun and Curlin, and somehow, walked away with $440. I was completely convinced, and I think Bryan was, too, that somehow, some way, it had something to do with The Hat.
** Derby, 2007 **
It was in 2009, while Bryan was living in Cleveland, that The Hat made it’s third, and most astonishing appearance. I believed, after 2007’s win, that one could not get selfish and simply wear The Lucky Hat every year- such greediness would diminish its magic. I waited the obligatory two seasons before I wore it to Churchill Downs with my girlfriend. All day, I had had a feeling about Mine That Bird, and, being several hundred dollars up from an exacta on the Oaks the day before, got a little brazen, and threw down $50 to win. My girlfriend thought I was crazy, but the bet was made, and I’ll be dammed if that horse didn’t streak to the finish as if he was on fire! I walked away with $2,580 dollars, again convinced it was all because of The Hat.
** Derby, 2009 **
Of course, the crazy win on Mine That Bird did not go unnoticed. My mom was the first to demand a go at The Hat, asking if she could don it to the Oaks in 2010. Being the assumer of the magic of the whole thing, I determined that it could easily be worn two years in a row- as long as it was worn by two different people. So, in 2010, Mom gave it a go, and could not lose the entire day!
The next year rolled around, however, and both my mom and dad decided to join Bryan and I for the Oaks. Instead of choosing a hat from my collection or buying one for herself, she elected to wear The Lucky Hat for the second year in a row… And didn’t win a penny!
Instead of donning it myself the following day, I decided to let the luck rest for a few more years. Then, on Derby Day, 2013, one of the coldest Derbys I remember, I made a last minute decision to doff the breezy silk dress and fascinator I was planning to wear, and threw on a black suit topped with The Hat and headed to the track. Trying to stay conservative, I remember making small bets all day- $2 across the board here, $5 to win there- still, no winning tickets. For the Derby race itself, we bet a $1 superfecta, and celebrated a win of over $28,000!!!! Until, of course, we realized we had two of the damn horses flip-flopped. The curse continued.
I vowed on the way home to give it five years, and not wear The Hat again until 2018.
** Derby, 2013 **
So now, she rests, sleeping happily, as I’m assuming hats do, in her little white hatbox, snug in my basement. Every so often, I think of her, go downstairs and pop open her box to say hello, and to tell her that I haven’t forgotten her, that her day is coming again.
Two years down, Lucky one. Three to go.
