Kentucky Derby Style: She Belongs.

About a month ago, I shot some Kentucky Derby style content on a private jet. (Definitely NOT my jet!) The shoot was part of an auction package some friends and I won at Misters for MS, a fundraiser here in Louisville for the National MS Society. While I know that not everyone would get excited about a fashion shoot on a PJ (as the cool Succession kids say), I saw it as an opportunity to have some fun photos taken with people I enjoy in an environment I wouldn’t usually have access to. Do it for the content, baby!!! (And the friend time, of course! It was so much fun.)

Sidenote: I’m on the planning committee for Misters for MS and you should definitely come to this year’s festivities. Or sponsor! Or donate a high-value item/package we can use in our live auction! For any of it, feel free to reach out to me anytime.

It’s this photoshoot that I was referencing in my last post about the hot mess experience of trying to find an outfit that really reflected how I wanted to look. The challenge of reconciling my vision and the very, very limited plus size options available was maddening. I hope you’ll read that piece if you haven’t already. It will give you a much deeper look at my mindset going into this experience, as well as the transformational power of clothes.

I use clothes and style as a way to show myself that I belong. That I am someone worth seeing. That I am more than my size. That I can stand out and not shrink. I can take up space.

It’s more than just a dress.

When I saw the photos from the shoot, it was like I was looking at someone else. I looked at her and she looked like she belonged. While fashion is subjective, I thought the person reflected in the photos was chic, sophisticated, full of confidence, and someone who understood style. I could see these photos in a Derby editorial or on a “what they wore” list. I then realized that it felt so novel because I couldn’t recall seeing plus size bodies in this context. When you’re my size, you notice these things. It’s like spotting a unicorn. And who doesn’t want more unicorns in the world?!

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Note: As I am about to delve more into the social/fashion aspects of this event and everything that surrounds it, I recognize that there are many complex issues at play. Privilege abounds in much of this hullabaloo, and there are class, race, and ethics situations that are entwined in a big knot that also happens to be a tremendous amount of economic impact to our city.

For those unfamiliar with the fashion spectacle that is the Kentucky Derby: Here in Louisville, it isn’t only about the two fastest minutes in sports. The first Saturday in May is the *main event,* but it is also the reason for the season.

Yes, season.

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The events around town that revolve around the Kentucky Derby start in early March – 2 months before race day. Many people who participate don’t even go to the races, but it’s prime social event time. A time to see and be seen. Those interested in the festivities begin penciling in parties, fashion shows, fundraisers, and more even earlier than March. Milliners work feverishly to meet demand, and boutiques and brands reveal their Derby-related wares and styles that are worthy of the spectacle. It’s all very fashion-forward, which makes it fun for someone like me who loves expressing myself through fashion. It’s also fun to prove to the rest of the world that Kentucky contains multitudes beyond Kentucky Fried Chicken and the stereotype that we don’t wear shoes.

It’s glitz, glam, a lot of bourbon, and a reason to wear fantastical headpieces. It is so fun to have a reason to wear artwork on your head. I think we should have more of that everywhere. But then again, I love any reason to accessorize.

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If you look at the fashion editorials — local or national — that are held up as the epitome of Kentucky Derby fashion, you won’t find many visibly plus size women. This year, the local lifestyle magazines and their beautifully produced Derby fashion editorials didn’t include anyone that I perceived as above a size 14. Perusing the galleries of Town & Country, Vogue, Southern Living, and Garden & Gun yielded hundreds of photos, with maybe 5 or so people above a size 14, but none that I’d classify in the 18+ size range. Considering 67% of American women are size 14 or larger, the math ain’t mathing.

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Locally, the lack of representation might be because the stores that are providing styles for the models don’t carry plus sizes. Nationally, the coverage is mainly street style photos/snaps from the event organized in large photo galleries with headlines like “The best fashions at the Kentucky Derby.” Given the 155,000 people in attendance, I can’t help but wonder if this exclusion is due to anti-fat bias. I know there are many stylish women of all sizes in attendance at the Kentucky Derby. If, in the eye of the editor pulling together the select images, big doesn’t equate to fashionable, they’re not going to be in the gallery.

It might not be an intentional exclusion, but when we’re operating in a world of conventional beauty standards where smaller is perceived as more attractive and the beauty-setters of the media world are in charge of selecting what they show, it feels like a choice.

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Also a very specific-to-me thing: the “influencer” invites and partnerships surrounding this time of year can reek of high school popularity contests. I suppose this is with all partnerships all year long, but around Derby season, it’s super noticeable when it’s all going down within a 10-mile radius of where I sit. At home. Without heels on. Maybe sleeping. Or reading a book. So maybe it’s a win for me after all! 🤷🏻‍♀️

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There are many times when I avoid places because I think I probably won’t fit in. Or even fit, because size accessibility is a thing. It’s gotten better throughout the years, but there are always hills and valleys in the search for confidence. Visual representation might seem trivial, but there is so much power in seeing someone like you — or friends and family — represented. We can all use a reminder that we belong.

Many thanks to The Hat Doctor, Ilana Kogan, for providing the absolutely stunning fascinator and for being part of the fun day, along with my friend and fellow Misters for MS committee member, Debra of Debra Locker Group.

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Ilana, Debra, and Me (obviously!)

Thank you to Crew Aviation Jets for the generous donation of this auction package to Misters for MS, including the skills of the immensely talented Andrea Hutchinson behind the camera. Makeup by Cassie did a killer job on my makeup!


Dress, ELOQUII (also available in other colors)
Fascinator, The Hat Doctor – she has really incredible pieces!
Shoes, old – similar
Earrings, Lele Sadoughi
Sunglasses, DIFF Eyewear (from my HSN collaboration here)

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Photography: Andrea Hutchinson
Makeup: Makeup by Cassie
Location: Crew Aviation Jets

Want more Kentucky Derby Plus Size Outfits and style? I have a lot in my archives!

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