Which Derby fashion will finish first? | Opinion | Pittsburgh | Pittsburgh City Paper

Which Derby fashion will finish first?

I am a sucker for all things Derby: Derby pie, Derby hats, and naturally, the Kentucky Derby. It’s kind of odd that I have a fascination with the Derby because I have a deep fear and hatred of horses.

Even as a child, my favorite part in The Godfather was when the movie producer found the dead horse head in his bed. (Not sure if it’s worse that my parents let me watch that film as a child or that I enjoyed severed horse heads.)

But even though I hate horses, I love the Kentucky Derby. Why? One reason only: the fashion. I love the bright pastel colors and the gingham prints. I love the hats, loafers, and bow ties. It’s the kind of attire I imagine Truman Capote sporting.


Yep, it’s true. I am obviously more interested in what is deemed “men’s fashion.”

I need to make something clear: I was raised by two amazing humans who never put restrictions on my clothing. Since I was a toddler, I was permitted to wear whatever I wanted without any gender expectations.

This leaves me to my dilemma: What do I wear to the Kentucky Derby? Not that I can afford to go, mind you; however, it’s on my bucket list so I plan on attending before I die.

I’m not a fan of the Southern belle attire. I hate big hats; I prefer fedoras. I do not like heels or sandals; my dress shoe of choice is a loafer. I’ve seen women wear rompers in lieu of a dress, but I can confidently say that I can’t hold my urine in long enough to safely wear a romper in public.


I guess I need to know how Ellen DeGeneres dresses to the Kentucky Derby to get some insight. I’m not going to be forced to dress in a way that makes me feel uncomfortable, especially if I’m pounding bourbons in the hot, Southern sun.

I grew up idolizing the fashion of Katharine Hepburn, Diane Keaton, and Frances McDormand. I think these women would prefer a bow tie to a floral fascinator.

I just hope that in 2019 we can move forward with even some of our favorite Southern traditions. I would hope a woman wearing a fitted suit, paired with a button down, an ascot, and loafers would not offend the other attendees.

Frankly if it did, the only other outfit I would consider wearing at this point would be a horse costume sans head. Don’t mess with me, Kentucky. Clothes are like bourbon; they're for everyone.

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