Racing and Rompers- Keeneland Trends Fashion 101

Kentucky Derby week is here! and before all the hats and bows and horses come to play, the nearby races in Keeneland give us an idea of what to expect, and a taste of luxury for those who can't make the main event. We went down for the weekend under the theme "Pink Pony Club" to get a handle on what everyones wearing, oh and the horses too.

My Keeneland Pink Pony Club outfit

So. Most importantly, my outfit. Although I spent all day roaming different Cincinnati boutiques, I ended up settling on this dress from Amazon ,which, I most definitely paid for as it BROKE 2 hours into the tailgate. However, I had the safety pins from pinning the adorable bows onto my boots, also from Amazon , so I was able to pin the dress together and cover the damage with the denim jacket. This is why we shop small business ya'll, they do product quality checks. Either way I still felt cute! And seemed to be pretty on trend, which brings us to why you are all here, the most popular trends I saw at Keeneland in 2025.

• Midi Dresses Midi-length dresses were everywhere at Keeneland this season. Flowing, elegant, and perfect for springtime breezes, these dresses struck the perfect balance between formal and relaxed. Popular choices included soft pastels, polka dots, and delicate prints.

• Floral Prints Keeneland was in full bloom, and so were the outfits. Floral dresses — from tiny daisy patterns to big, bold botanical prints — were the unofficial dress code. Bright colors like coral, sunflower yellow, and sky blue dominated the flower fields of fashion.

• Corseted Tea Dresses Vintage charm made a major comeback with corseted tea dresses. Think structured bodices, flared skirts, and romantic detailing. Many racegoers paired these dresses with dainty gloves and classic pearls for a truly timeless look.

• Wide-Brim Hats and Fascinators No trip to Keeneland is complete without a statement hat. Wide-brim straw hats decked out in ribbons, feathers, and silk flowers were a must-have. For those who preferred a lighter touch, intricate fascinators with netting and crystals offered a chic alternative.

• Seersucker and Linen Suits (for Men) Men brought their A-game with classic seersucker and linen suits, perfect for the warm weather. Light shades like powder blue, tan, and soft green ruled the paddock, often paired with bold bow ties or playful patterned ties.

• Pastel Color Palette From mint green to blush pink, soft pastels set the tone. Outfits looked fresh, airy, and right in tune with the season. It wasn’t just limited to dresses — accessories, shoes, and even nail polish followed the pastel trend.

• Block Heels and Comfortable Footwear Navigating Keeneland’s brick paths and grassy areas requires smart shoe choices. Block heels, low wedges, and stylish flats were the secret weapons for fashionable, blister-free afternoons.

• Statement Earrings and Accessories Oversized earrings, chunky bangles, and brightly colored clutches added the perfect finishing touches. Accessories at Keeneland weren’t just an afterthought — they were conversation starters.

• Puff Sleeves and Ruffle Details Many dresses had fun, feminine puff sleeves or tiered ruffles, adding a little extra drama and volume to race day looks. These small details made simple silhouettes feel extra special.

• Coordinated Group Looks Friend groups and couples often dressed in matching or complementary colors, making their outfits pop even more in photos. Coordinated pinks, blues, and florals created a unified, stylish vibe among the crowds.

Also important to note is my cutie pie cousin's outfit, following the Pink Pony Club, FYI boyfriends are not required for the look ;)

Planning a trip to the derby? Well we also found you an online boutique if you find yourself in need of an outfit that has the perfect thing :). Be sure to check out Shop Weekend Club