I Attended the 152nd Kentucky Derby—Here's What Fashion People Actually Wear to the Races
With Golden Tempo leading, the stadium cheered as the bay coat racehorse crossed the finish line. The 152nd Kentucky Derby victory marked several firsts: Cherie DeVaux became the first female trainer to win the Derby, jockeys Jose Ortiz and Irad Ortiz Jr. were the first brothers to finish first and second, and it was a historic moment for me as it was my first time at the races.
I was invited by Longines, the official timekeeper of the Kentucky Derby, and I experienced firsthand why it is dubbed "the most exciting two minutes in sports." Two days of nonstop excitement, the Longines Kentucky Oaks Day and the Kentucky Derby Day, supplied enough joy until next year's Run for the Roses.
On the Thursday before, given the number of hat boxes on my Louisville-bound flight, I should have been prepared for the fashion show to come. Side note: Churchill Downs might as well have its own fashion week designation. I had so much fun spotting the next It-watches, designer dresses, premium handbags (imagine this: a Bottega Veneta Andiamo and an Hermès Birkin on the same arm), and, of course, the fascinators. While the word is a lot of fun to say, these gravity-defying toppers are no joke. Feathers, flowers, polka dots, lace, bows, you name it, I saw it. Whether DIY or designed by a professional milliner, the hats, dare I say, are just as important as the horses. The Hat Girls and Ilana Kogan are local Louisville milliners who provide many of the extravagant head dressings.
If this year's historical headlines have you thinking about a trip to Louisville, consider this your guide to Kentucky Derby outfits. Keep scrolling to find out what fashion people actually wore to the races—from unexpected trends to standout wristwatches (hello, Longines DolceVita) to cool sets to It-girl brands (ahem, Alexia María, Smythe, Khaite, and Scanlan Theodore).
152nd Kentucky Derby Day
While bright, colorful looks are expected at Twinspires, coal-black and alabaster-white were surprisingly common themes among the Louisville crowd. Whether it was a part of a monochrome 'fit (yes, there's a way for dark colors to feel light-hearted and for all-white suitings to garner a presence) or a mix of both (think polka dots and textured tweeds), the style set embraced this unexpected duo for the 152nd Kentucky Derby.
Fashion creators Victoria Herran and Mary Glenn McElveen combined timeless style with a contemporary sensibility. Chad Alexander and Georgia Benjamin brought out the Longines starting line-up. (We'll talk about the Hydroconquest—don't you worry.) And me? I delivered retro elegance with an NYC flair. Ahead, read how we each approached dressing for the Derby.
Victoria Herran
"The Kentucky Derby has such an electric energy. You really feel it from the moment you arrive. The fashion leans more dramatic these days, and it feels so extravagant, with everyone dressing to impress. I loved seeing how people pushed the boundaries while still honoring tradition. I know black is not the most traditional choice for the Derby, but I loved the contrast, and it really stood out in a good way, surrounded by all the pastels. Everyone was so kind and complimented me on the look, which made it even more fun to wear," said Herran.
The Miami It girt went on to say, "I wanted my look to feel structured and refined, so I wore a silk-and-wool Alexia María three-piece set with a peplum top, cigarette pants, and a convertible skirt to bring in that classic Derby volume. I paired it with a Gabriela Hearst bag, Christian Louboutin heels, an all-black fascinator from Etsy, and my Longines DolceVita in 18 karat yellow gold with diamond detailing. It felt like the perfect balance of timeless and modern, which is what makes Derby style so iconic. Watching Golden Temple come from the back of the pack was incredibly emotional to watch, and I loved seeing Cherie’s reaction to her win. Truly one of the greatest experiences I’ve ever had!"
Mary Glenn McElveen
"The Derby is where the fashion really takes on a life of its own, and I wanted my look to reflect that, so I leaned into something more statement-making while still keeping it timeless. From the energy of the races to the incredible style moments everywhere you look, it’s truly unlike anything else. Experiencing it with Longines made it even more meaningful," shared stylist and wardrobe consultant McElveen.
Chad Alexander
"Attending the Kentucky Derby with Longines was an experience of a lifetime. From on-track and paddock access to the VIP hospitality of the Mansion, it was the ultimate bucket list moment," remarked Alexander, who is known for his educational watch-focused content.
He clarified, "For the fit, I wanted chic with flair. My inspo was if A$AP Rocky attended the Derby. I went with a full linen look from Sandro: wide-leg trousers, a strong double-breasted jacket with structured shoulders, and a striped shirt and tie for a subtle pop of color. On the wrist, I kept it sporty with the new HydroConquest from Longines."
Georgia Benjamin
"If Ascot is the polite older cousin, the Derby is the opposite: louder, hotter, more flamboyant, and somehow convinces you to bet on a horse named after a 90s sitcom character before you've finished your first mint julep. People really pulled out all the stops. It wasn't just sharp tailoring and beautifully made suits; it was the most elaborate hats I have ever seen in my life. Mine was relatively uncomfortable and significantly larger than a dinner plate, and it still had nothing on what some of the women were wearing. Dare I say wonderfully extra, in the best possible way, where nobody cares, and everyone is fully committed to the spectacle," shared watch lover Benjamin.
Josephine Hadjiloucas
As featured in our Go Sports! Style Playbook, my look is reminiscent of Old Hollywood icons like Audrey Hepburn, with a touch of city charm from New York's own Jackie Onassis-Kennedy. I've been waiting for an excuse to wear my Smythe Cropped Sleeve Mini Jacket, and lucky for me, they had the perfect pencil skirt to match. I picked up my hat from Mains de Vapeur, a NYC-based millinery founded by Mariela Alexandra. From the bridal collection, I'm wearing the Cleo—a wide-brim velour felt fur hat with silk ribbon.
The stark white hat brought out the softer tones in the textured tweed set, even more so when worn with a white clutch. This one is from COS. I finished the look with my La Grande Classique de Longines, a timepiece I wear both every day and for special occasions. I was quite comfortable in this heavyweight set; even local Louisianians had alerted us that the weather was unseasonably cold. I stayed cozy and chic while watching the horses at the Paddock stalls.
Longines Kentucky Oaks Day
The Friday before the Derby Day is the Longines Kentucky Oaks Day. Affectionally called the "Lilies of the Fillies," since the ceremony awards the winner of the 3-year-old fillies race with a garland of lilies. The dress code is pink to support breast and ovarian cancer survivors and raise awareness. Follow that, and you'll fit right in. Here's how fashion people dressed on theme.
Victoria Herran
"Oaks Day was a sea of pink in the most beautiful, intentional way. It is such a powerful tradition that blends fashion with meaning while supporting breast and ovarian cancer awareness. The entire experience felt so celebratory, from the energy around the races to how fully everyone embraced the theme," said Herran.
Here's Herran on what she wore to Churchill Downs: "My coral pink Acler set felt like a modern take on the tradition, and I styled it with a soft pink statement fascinator, a Louis Vuitton Capucines bag, and a Shop Alexis shawl to add dimension and movement, along with a Longines watch for a polished, timeless finish. I love how Derby fashion allows you to be expressive while still feeling elevated. There is such a balance of elegance and individuality. And as someone who rides, getting to watch the horses compete at that level made it even more special. I was especially excited watching Always a Runner. She was incredible to watch and really owned the moment. Watching the race from the grass track was easily one of the most exciting moments of my life."
Mary Glenn McElveen
"Oaks Day felt like the perfect introduction to the weekend. There's elegance and femininity that really define the day. I wore a draped white dress with soft pink accents, which felt like a natural nod to the tradition while still keeping it modern. Being there with Longines added such a unique perspective, especially getting to step down onto the track for the final race, which was such an unforgettable, behind-the-scenes moment," explained McElveen.
Chad Alexander
Alexander, another person shocked by the "pink out" of Kentucky Oaks, shared his thoughts: "Being amongst a sea of pink at the Kentucky Oaks was a pinch-me moment in itself, but the most surreal moment came during the race—standing just feet from the horses on the inner track at sunset, watching them gallop to the finish line with a backdrop of 170,000 spectators in pink."
"Pink isn't exactly a staple in my wardrobe—I tend to live in darks and neutrals—so pairing it with a dark brown suit from SuitSupply wasn't the easiest challenge. But I think I pulled it off. Good rule of thumb: a little goes a long way," shared Alexander.
Georgia Benjamin
"Oaks Day is the Derby's slightly cooler younger cousin: whimsical, magical, gleeful, and drenched in pink from the second you walk in. The girliness across Churchill Downs was something else. I'm not even a pink girl, and they had me drinking pink drinks all day long, and I have genuinely never been happier. Special shout-out to the men who turned up in full pink regalia, truly spectacular commitment. The whole thing felt like a very chic excuse to lean into the whimsy and watch extraordinary fillies run very, very fast," commented Benjamin.
Josephine Hadjiloucas
The minute I tried on the Scanlan Theodore Resin Pencil Dress, I knew it was Kentucky Oaks–bound. Only then, I wish I knew, I would be crossing the track and watching the Oaks Day race from the inner turf, perhaps I'd back a different pair of heels. The raspberry hue of the resin dress was the perfect addition to the light pinks and fuchsias that flooded Churchill Downs. I turned to Mariela at Mains de Vapeur again to find me the perfect topper. After trying on many a pillbox hat or a beret, we landed on a floppy, wide-brimmed black hat with a white silk gazar flower pin.
First, I was hesitant, worried about the black hat with the berry-toned dress, but once I added my black strap Longines Dolcevita, a beaded evening bag, and block heels, I knew Mariela's choice was intentional. The shadows created by the woven sun hat mimicked the dress's resin texture. It was absolutely divine. I felt beautiful.
