Lexington, Ky.—April 21

 Every award show season, the most-asked question on the red carpet is, “Who are you wearing?”

There’s a similar vibe during the last weekend in April at the Kentucky Horse Park as riders trade their breeches for more dapper attire at the first Land Rover Kentucky Three-Day Event horse inspection. In true red-carpet fashion, an often-asked question becomes, “How’d you pick out your outfit?”

Some are planned months in advance while others are thrown together at the last minute, but the stories are always fun to share.

Leah Lang-Gluscic and AP Prime. Lindsay Berreth Photos

In her previous trips to Kentucky, Leah Lang-Gluscic has kept her outfit fairly traditional, but this year, she decided to switch it up.

“I went to Zara two weeks ago and just picked something I liked,” she said. “I’ve always done something super traditional here, and I never win [Best Dressed], so I was like, I’m just going to wear something I’m going to wear again.  I went shopping, had fun. It’s the first time I’ve ever bought anything new for this.”

Though the black top showed off her midriff—toned with help from daily 6 a.m. hot yoga sessions—it wasn’t ideal for the brisk, breezy 41-degree weather.

“When we were walking [AP Prime] over by the barns, I was debating whether or not I’d jog in my winter coat!” she joked.

Valerie Vizcarrondo Pride and Favian.

Few people’s trip to Kentucky were quite as dramatic as Valerie Vizcarrondo Pride’s, whose truck broke down en route from her base in Harwood, Maryland. Thankfully, replacing a sensor was enough to get her, five-star mount Favian and his support miniature horse Theodore back on the road.

“That was, like, the bleakest moment. I had the pedal down on the truck, and it was going 3 miles an hour in the mountains,” she said, admitting she did break down and have a little cry at one point. “I was just like, first of all, it can’t be happening, and then it was like this is not going to stop us. I can’t believe this is how it’s all supposed to end. But here we are—tremendous support from all sorts of people to get us here—and the truck is here, we should also be able to get home!

“Hopefully it means we’ve proved we can rise to the occasion in any challenge, and now we can just let that spin it, and smooth sailing from here now through the rest of the week. That’d be great.”

Luckily, her jog outfit was far less complicated than her trip to Kentucky. Her bright pink dress was made by Gretchen Scott and is designed to be rolled up and packed without wrinkling.

“It’s a lot of pressure, when you ride a horse that we nicknamed ‘Black Beauty,’ so it was a really a chance to get to wear something that would complement how beautiful he is,” she said.

Emily Hamel and Corvett.

Five-star rookie Emily Hamel had to make a few last-minute changes to her outfit plan after a storm left 2 inches of snow on the Kentucky Horse Park grounds this morning. She donned a cream-colored jacket with a fuzzy lining— equal parts fashion and warming function—and paired it with brightly colored accessories and boldly patterned capris.

“It’s kind of a last-minute outfit because [of] the weather,” she said. “I had some other things planned, but it actually kind of came together. It’s like various people’s little bits and pieces. My friend Sarah Jennings let me borrow the scarf, and my friend Amy Peloquin let me borrow the earrings.”

Boyd Martin and Long Island T.

While men’s attire is fairly standard—you can’t go wrong with slacks, a sport coat (or maybe a puffy jacket!) and a nice tie—Boyd Martin’s blue tie paid homage to his Australian upbringing. It featured an aboriginal pattern and came from his father, Ross Martin.

“I don’t have many ties, so I seem to wear it at every event,” Boyd joked. “It seems to be in my garment bag every event, so I’ll keep wearing it until I lose it.”

Lauren Nicholson and an unimpressed Vermiculus.

We all know someone for whom fashion is not a priority. Lauren Nicholson is that person, but luckily for her, she’s got a team ready to help her pick the perfect outfit.

“The Hound and Hare dressed me from head to toe. They’re awesome,” she said. “They dress me every year, and I love them. Nobody would say I’m the most stylish. If I look good, it’s probably because somebody else dressed me.”

Here are a few more of our favorite looks.

Tamie Smith and Mai Baum.

Ema Klugman and Bendigo.

Liz Halliday-Sharp and Deniro Z.

Karl Slezak and Fernhill Wishes.

Daniela Moguel and Cecelia.

Jennie Brannigan and FE Lifestyle.

Will Coleman and Dondante.

Fylicia Barr sported an outfit she had picked out for last year’s event before it got canceled as she jogged Galloway Sunrise.

Sharon White and Cooley On Show.

Marilyn Little and RF Scandalous.

The Chronicle of the Horse will be on-site all week for the Land Rover Kentucky Three-Day Event bringing you reports from each round of competition, beautiful photos and stories from the competitors. Follow along with all of our coverage here, and be sure to read our May 17 Kentucky Results issue for more in-depth coverage and analysis of the event.