A newcomer tries, but ultimately fails, to 'get' Derby madness [Louisville newbie]

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KY Oaks

“I feel silly,” I admitted, looking up at the brim of the vintage white had I’d purchased at Pink Door Boutique the day before. My thin hair and the angle of my ears don’t make them a natural fit, so as a rule I don’t do hats.

“You won’t feel silly once you’re at the track,” my boyfriend reassures me as I get into his car. “You look fine.”

He’s right, of course. I look fine. I look better than fine, really. I will go so far as to say I look gussied up. I have never used the term “gussied up” until this week, but it seems appropriate. After all, I have never experienced something quite like this week: my first Kentucky Derby season.

A local invited me to attend Kentucky Oaks, which everyone in Louisville knows about but I had to Google. I graciously accepted and kept my mouth shut when it was explained we’d be hanging out in the infield and would likely never see zero horses, let alone races. In my world, that doesn’t sound like fun, but I’m not in my world. I’m in Kentucky. So I went with it.

Walking down Third Street, I passed Derby season entrepreneurs selling their yards as parking spaces and one unfortunate guy just trying to drive to work. I saw a few gussied up women standing on porches and smiled. This is kind of cute, I thought.

Then, I hit Central Avenue.

The sidewalks were packed with gussied up men and women – big hats, lots of pastels and seersucker as far down the road as I could see. I literally stopped, overwhelmed by this sea of style and purpose. To procrastinate actually stepping foot in Churchill Downs, I buy a $3 burger from some kids raising money for leukemia and lymphoma research. Small talk ensues about the idiot proselytizing across the street. I wonder why all Catholics are going to hell, but I’m not about to ask.

Eventually, I make it to Churchill Downs’ main entrance, also known as Gate 1. People here are taking photos with the iconic twin spires in the background, and an old timey band is playing for tips. This feels regal, and suddenly I feel bad for wearing sandals instead of heels like all the beautiful women here.

Then, I realize I am at the wrong entrance. This is Gate 1 Percent. I have to enter through Gate 3, with the other infielders and their coolers, lawn chairs and sensible shoes. So, like a fish swimming upstream, I walk opposite the immaculately dressed until I approach Gate 3, which is unceremoniously located right next to a PNC bank.

My heart sinks quickly as I realize there is no dress code here. People are wearing cutoff jean shorts, Birkenstocks and football T-shirts for teams that aren’t even in Kentucky. One vendor outside is selling “If you didn’t come to party, take your bitch ass home” T-shirts but most are just selling cans of beer. Admittedly, the dressed up outnumbered the dressed down, but some of the mystique was gone. I probably should have known not all Derby fashion made the In Touch roundups, but alas. Newbie lesson learned.

Evacuating the infield, under the watchful eye of people with real seats.
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