As an Editor who lives for the New York fashion scene, I wasn’t sure what to expect from my first Kentucky Derby. I spent the entire day with my eyes glued to the outfits instead of the track (working gal!) to bring you the best of the best. From classic ruffles to dresses built from flowers, the girls really went all out. Here is everything that caught my eye.
If there was one trend that was inescapable, it was the drop-down waist corset dress. They are incredibly flattering (they snatch you in all the right places!) and they were everywhere at the derby. I saw them in every primary color, but pink was the obvious winner for Oaks Day.
Most of the girls I spoke to were wearing House of CB—just a pro-tip for anyone looking to snag one: their sizing runs very small, so definitely size up! I even fit the trend myself in my Miss Circle drop-waist mini.
Ava is a Creative Editor at OOTD. She moved to New York City at 18 to pursue a career in fashion and now covers your favorite fashion figures, events, and trends.
Red is everywhere right now, and naturally, it dominated the Derby. While some opted for subtle pops of color, others leaned into the full monochromatic look. My absolute favorite was a handmade rose dress—her mom actually used real roses to construct it!
The elegance was off the charts, especially the asymmetrical red dress styled with a black fur coat and a quilted Chanel bag. It felt like a high-fashion take on the "Run for the Roses" tradition.
Polka dots have been a big trend in 2025 and they’ve officially carried over to 2026. There is just a timeless feel to polka dots or stripes; it adds a fun flavor to an otherwise boring piece. I saw polka dot dresses in literally every color.
One girl pulled off this classic look perfectly with a white sleeveless polka dot maxi dress and black stilettos. But the look that almost made me shed tears? These three sisters matching with their mom! They all wore different colored polka dot dresses and were way too adorable. They even showed me their matching nails to go with the dresses.
Ruffles and lace were the "wow" features that made me linger a bit longer on the details. I met one girl in a stunning blue skirt featuring ruffled florals along the hem that caught my eye immediately. Another woman looked like she stepped out of a period piece in a gorgeous pink and white striped ensemble with ruffled tiers and delicate lace trim.
I also spotted the Elliatt Rova One-Shoulder Minidress at least once every ten minutes. At first, I thought I was seeing the same person repeatedly, but it turns out it was just the dress of the derby.
A look I will always die for is the feminine suit. It’s classy, versatile, and was the smartest choice for the 50-degree weather at the derby this year.
One standout was a pinstriped suit from Naked Wardrobe, styled with a bold red tie for that perfect masculine-meets-feminine edge. I also loved a full lace suit worn by a personal stylist; it was delicate, sophisticated, and matched her accessories perfectly.
Even with the recurring trends, there were so many unique, inspired looks that I wouldn’t have seen anywhere else. I always love a good reason to dress up to the tens, and I had so much fun spotting the little details. I’m leaving the derby feeling inspired—and I’ve already started a mood board for my outfit next year.
