The Jetsetting Fashionista: Kentucky Derby, the Grit and the Glamour



The plane ride to Kentucky was uneventful. And that’s what you want in a plane ride. Uneventfulness. Normalcy. But both of those qualities evaporated as soon as I touched ground at the Derby.

We kicked off with Thurby (the Thursday before the Derby), which is typically for locals. You can see the Thursday races for $30 instead of $1,500. 

Kentucky minions, we welcome you to Thurby! (Doesn’t seem condescending at all, right?) Well I went and I minioned. It’s basically the same thing as the Derby, minus the 100K frat boys celebrating their 20-year anniversary. I mean, let’s face it, any man wanting to dress up and wear a hat was definitely a [fill in name of fraternity here]. Or maybe I’m just salty that I can’t get my Seattle-born husband to don a seersucker suit and join the fun. As for me, I brought 17,000 outfits and 489 hats, so I was down for any occasion the Derby threw at me. Bring it, KD!

This year the Derby was “all inclusive”. Yay! Food and drinks are FREEEE! Well, turns out it was about as free as everything else in life. An extra $300 gets you a place in a 30-minute line that ends with the lady in front of you taking the last four chicken tenders. My chicken tenders. I had laid claim to them! I even talked to some guys who were eating hotdog BUNS. Just the bun. That’s all they could find! “All you can eat” apparently made everyone in Kentucky ravenous, and try as it might, the Derby, bless its equine heart, just couldn’t keep up with the demand.  

 The next day was Kentucky Oaks, the Friday before the Big Day. We bought tickets ahead of time so we were set. All dressed up and some place to go, we headed to Churchill Downs. 

It was crowded. And it rained. (A special shout-out to the Derby gods that we’d bought covered seats.) 

The horses raced. Mine lost. Mine always loses. Except I knew that Taiba was going to win the Derby. So my cash day was coming on Saturday, right? And who cares anyway? I was at the Kentucky Derby! Rain or shine, win or lose, hungry or full of hot dog buns, the excitement was palpable.

As fun as it all was, the event I was most looking forward to (correction: strike “looking forward to” and add “fervently salivating over”) was the Friday night gala Unbridled Eve. It’s literally dripping with celebrities. (And maybe a horse racing enthusiast here and there.) Not that I’m celebrity crazy or anything. 

OK, I can’t lie to my beloved readers: I AM CELEBRITY CRAZY. Unbridled Eve was my Mecca. 

I’m a product of the 80s, so let’s just say I stepped into my 80-90s Sitcom Paradise. I’m talking AC Slater, Clarissa (or Sabrina), as in Explains It All (or The Teenage Witch). And Micheal Gross, the dad from Family Ties.

Michael Gross and Emily.

So who do you think my favorite was? Heart throb Mario Lopez? One would think. Oh, but it isn’t so. It was Micheal Gross. Why? Well, for that story, let’s rewind 30 years or so to the Court Square in downtown Newnan. Specifically, our local Lee-King Pharmacy, complete with a soda fountain serving up the best milkshakes in town.

The year was 1991. Eleven-year-old Emily Chandler (that would be me) was heading into Lee King for a chocolate shake and a grilled chicken salad sandwich, lovingly prepared by a sweet lady with the name of—I’m not making this up—-Emily Chandler. (Old-school Newnanites can attest to this.) 

Turns out, they were filming a movie inside. As I was walking into the drug store, the “dad” from my favorite show was walking out. 

I was taken aback. And it showed. With a look of total surprise, I gasped and pointed. And Mr. Family Ties gave it right back. The same surprised expression. The same point of the finger. It was a moment that has stuck in my mind for 30+ years. 

Now let’s zoom back up to 2022, where Michael Gross and 42-year-old Emily Chandler (now Westergreen) are standing on the red carpet at Unbridled Eve, recreating for the camera those gasps and those mutual points … from almost a third of a century ago. It was a full-circle moment I could never have anticipated.

The End.

Oh, wait, did I mention the next day, I went to the Derby?

Emily Chandler-Westergreen has a passion for fashion. The founder of Underground Runway, a boutique-with-a-twist, she’s a regular fixture at New York Fashion Week, Sundance and other celebrity-drenched events—though none more gratifying than time spent with her family.

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