Ranking Dylan Dreyer's Head-Turning Kentucky Derby Looks

The 152^nd Kentucky Derby will take place at Churchill Downs in Louisville, Kentucky, on May 2, 2026. It's the first of three races in which three-year-old thoroughbred horses compete for the coveted Triple Crown Trophy, which has only been won by 13 horses since its inception in 1919. As has been the case since 2017, Dylan Dreyer will be on hand to cover the event for "Today" and NBC Sports.

"It started that I would come to Louisville for Saturday's 'Today' show and Al Roker would do Fridays and then one year his flight got canceled and I was already in town so I jumped in and did his Friday shift," Dreyer told the Courier Journal in April 2024, adding that her full coverage of the event, often called the 'most exciting two minutes in sports,' evolved from there. "Now I am fully ingrained in the Kentucky Derby and I love it," Dreyer told the journal.

Although the Kentucky Derby has proven to be a fashion nightmare for some celebrities, Dreyer isn't one of them. No matter if it's rain or shine, Dreyer brings her own unique style to the Derby every year — including the required hat or fascinator — making her outfits definitely something to look forward to for her fans. With so many years and looks for each Derby under her belt, trying to rank Dreyer's best dresses wasn't easy. But it was definitely fun. 

While Dylan Dreyer has rocked some leggy looks, she's been to the Kentucky Derby enough to know attendees are expected to dress appropriately for the event. For men, suits are encouraged, and for women, dresses and, of course, the iconic hat, are basically required. For the 145^th running of the Derby in May 2019, Dreyer wore a blue floral dress with a high-low hem, beige sandals, and a coral fascinator. Although a perfect first-Saturday-in-May look, the dress is a bit on the casual side for the occasion.

When Dylan Dreyer covered the 144^th Kentucky Derby in May 2018, as great as her outfit was for the event, all the shades of pastel gave Easter Sunday vibes. Of course, this isn't a bad thing; just an observation. As she did in 2019, Dreyer opted for a floral-printed dress with a high-low hem, but this time she went strapless. While her hat, being more on the traditional side, isn't as exciting as some of her other headpieces for the Derby, it still proves Dreyer knew the assignment.

If you've never watched Dylan Dreyer's coverage of the Kentucky Derby, then you probably don't know that despite the race being only two minutes, she's in Louisville all weekend. In other words, she rocks a few different looks every year. For her second outfit of the weekend in May 2019, Dreyer wore a pink and navy floral dress with another high-low hem by Eliza J. Her gorgeous pink and violet fascinator looked like a bouquet and very much stole the show. But as beautiful as this ensemble was, it was also very safe.

It wasn't until the 2020s that Dylan Dreyer really hit her stride with Kentucky Derby looks. Although magenta is a color that might do more harm than good when you wear it, in regard to regulating your nervous system, all we see here is perfection. From the 3D floral embellishments on the tea-length Lela Rose dress, to the just-extravagant-enough wide-brimmed hat and matching platform sandals, for the 150^th Kentucky Derby in May 2024, Dreyer really outdid herself.

In 2024, Dylan Dreyer's Kentucky Derby looks were simply spectacular. Granted, it was the 150^th running of the iconic race, so naturally, you want to hit it out of the park, which is what Dreyer did. In complete contrast to the magenta outfit, Dreyer went for head-to-toe navy for her second look of the weekend. The strapless, full-length pleated One33 Social dress was an instant classic, not just in color but in design. Dreyer completed her look with a matching hat by Christine A. Moore Millinery, as she does every year, and matching heels.

While some of the comments on Dylan Dreyer's Instagram post regarding this particular Kentucky Derby outfit in May 2025 aren't exactly complimentary, the reason this Lela Rose look gets number three on our list is because Dreyer took a risk, and that's what fashion is all about. Between the full-length matcha-colored skirt, the pink and white plaid twin set, and the hat covered in feathers and a pink bow, Dreyer clearly isn't afraid to have fun. It's still sophisticated in its own way and adheres to the Derby rules, so why the heck not?

For the Kentucky Derby in May 2022, Dylan Dryer wore what she considers her favorite Derby dress and hat — at least that's what she wrote in the Instagram caption when she thanked everyone involved for making her 'feel fancy.' The Kelly green and floral satin dress with a sweetheart neckline and spaghetti straps by Eliza J. was the perfect color and design for Dreyer, and the coordinating hat by Christine A. Moore brought everything together perfectly.

While Dylan Dreyer has never really had any Kentucky Derby looks that were total misses, only recently have her outfits really started to shine. This fact became extra-evident in May 2025 when Dreyer rocked this winning look by Shoshanna — her fourth of the weekend — and absolutely stunned. Not everyone can make a one-strap gown work, but Dreyer does so effortlessly. Unlike past floral prints, this one feels more sophisticated because of the daintiness of the flowers, and the hat — although bolder in color — is the ideal complement, making this her best of the best.

As we said in the introduction, ranking Dylan Dreyer's Kentucky Derby outfits over the last 12 years was no easy feat. It wasn't just about how she looked in each one, but if the dress was appropriate for the occasion — and all those Derby rules — as well as whether it was fashionably and stylistically relevant when it was worn, and if it had something eye-popping to offer. Although Dreyer won't live down a certain on-air outfit, for the most part, because she sticks to classic pieces, she rarely makes a fashion faux pas.

In our opinion, all of Dreyer's outfits hit the nail on the head for the Kentucky Derby. While not every look will be loved by everyone, fashion is about taking risks. Although there's no guarantee that things will turn out the way you plan, from what we've noticed with Dreyer and her Derby choices, she's mastered how to dress for the occasion.