Dylan Dreyer’s Kentucky Derby fashion run kept rolling on May 2, 2025, when she showed off her second look of the weekend. The television host and meteorologist wore a dress with a peplum and giant dandelions, topped with a tall fascinator in a coordinating yellow shade and dangly earrings.
The look drew a split reaction online, with some Instagram followers praising the outfit and others calling it divisive. One wrote, “You had pink options but chose this for Oaks Day, where pink is the theme,” while another said, “It was a miss for me and for the purpose of the day. #survivors.” Pink on Oaks Day is meant to support breast cancer awareness.
Dreyer first became a familiar face on the live Kentucky Derby broadcast because Today hired her for meteorology, not fashion. Her role expanded after Al Roker had travel delays, and by 2024 she said the assignment had “snowballed” and that she was now “fully ingrained in the Kentucky Derby and I love it.”
That history helps explain why the scrutiny around her clothes has become part of the event itself. Dreyer’s 2025 Derby appearances included five different outfits, from a pink gingham shell and cardigan with a pale pink bow on her hat to a vibrant pink lace dress, a one-shouldered dress with multicolored flowers, and a yellow, green and black look with pink accents. She also noted that the hat with her bright all-pink outfit would shield her hair, and she shared another post showing her with a big umbrella.
The details mattered because the Derby has its own style code, especially for hats, and the event’s website even offers advice for people trying to nail the look. Dreyer’s hats were all bespoke, which made the reaction to her outfits feel less like casual chatter and more like a verdict on how much room there is for personal style within Oaks Day tradition. The answer is that there is room, but not enough to keep the audience from taking sides.
