A Look Back At Dylan Dreyer's 2025 Kentucky Derby Outfits

Even though "Today" initially hired Dylan Dreyer for her expertise as a meteorologist, she's branched out to become one of the talk show's richest stars. Dreyer's talked about parenting on "The Parent Chat" podcast from "Today," and, likely since she's sporty in real life, she's been a staple of the live broadcast from the Kentucky Derby. Dreyer's role at the event expanded when Al Roker experienced travel delays. "It just snowballed from there ... Now I am fully ingrained in the Kentucky Derby and I love it," Dreyer explained to the Courier Journal in 2024.

Fashion is a major component of the event, and the Derby's website offer suggestions to help people nail their look, especially when it comes to hats. In Dreyer's case, the styling workload is even greater. For instance, on May 2, 2025, Dreyer showed off her second look of the weekend — a dress with a peplum and giant dandelions. The "Today" host topped off the look with a tall fascinator in a coordinating yellow shade, and dangly earrings.

While some people praised Dreyer's look, it also proved divisive. "You had pink options but chose this for Oaks Day, where pink is the theme," remarked one Instagram follower. "It was a miss for me and for the purpose of the day. #survivors." The pink on Oaks Day is intended to support breast cancer awareness. Although Dreyer mentioned her earrings had a bit of pink in them, it's hard to discern in the pics, and it's certainly nowhere close to the vibrant pink ensemble she wore on another day of the festivities.

Dylan Dreyer wore five different outfits for the 2025 Kentucky Derby. For those disappointed by the lack of pink in her second outfit, Dreyer's first look included a pink gingham shell and cardigan, and her hat had a pale pink bow. The whole ensemble evoked an early-1900s vibe, which some fans applauded. Unfortunately, not only did the ankle-length skirt conceal Dreyer's killer legs, it was also pretty rumpled, leaving others unimpressed. "Too much southern bourbon???" joked one on Instagram.

Luckily, Dreyer's final three 'fits were positively received. Her third look, a vibrant pink lace dress and coordinating hat, was a fan favorite. The only confounding detail is that Dreyer didn't wear this ensemble on Oaks Day, when it would have been an optimal choice. Dreyer's been outspoken about breast cancer awareness previously, as she has an aunt who is a survivor, so clearly the cause is close to her heart. Dreyer's fourth dress was one-shouldered and featured multicolored flowers, including pink ones, and a touch of pink in the fascinator. Although her fifth 'fit only had a few splashes of pink in the yellow, green, and black dress, pink predominated the floppy, wide-brimmed hat.

It's possible Dreyer wore the dandelion dress on Oaks Day to stand out from the crowd. The wet weather on Derby Day may have also played a role in which 'fit she wore when, since Dreyer noted on Instagram that the hat with her bright all-pink outfit would shield her hair. Even so, Dreyer was seen with a big umbrella in another one of her Instagram posts. Since her hats were all bespoke and even some of the retail versions of Derby hats cost over $1,000, it's unlikely she would have risked getting them too wet.