Dylan Dreyer's 2019 Kentucky Derby Look Was A Total Hot Mess

"Today" and NBC News host Dylan Dreyer helped host the Kentucky Derby for her 12th year running in 2025. The world's biggest horse race draws in a massive crowd of over 150,000 people, but the most exciting two minutes in sports is not just about the horses. The annual race held at Churchill Downs in Louisville, Kentucky, is equally known for its high-fashion looks that include elaborate, custom-made hats that stun the crowd. While the celebrities and elite guests walk the red carpet to impress, that is especially true for Dreyer after hosting the event for over a decade. 

Dreyer's iconic Kentucky Derby looks are always a topic of conversation as she tries to outdo herself each year. Usually donning bright and floral patterns, she has offered some of the most eye-catching styles at the racing event. However, she will forever be haunted by her 2019 Derby look that was less than flattering. Even Dreyer's killer legs couldn't save this awful outfit, which included a bright coral hat that did not match the colors of her light blue dress. The outfit looked sloppy and thrown together last minute, deprived of the charm and elegance usually expected from her event looks. 

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On her 2019 Instagram post debuting her Derby look on the red carpet, users were quick to point out the poorly coordinated outfit. "Hat is bad! But you always look great," one user commented. "Not my favorite dress love the 1st one," someone admitted. "Nah. Not a fav," another candidly wrote in the comment section. Dreyer also shared a second Instagram post in the outfit alongside NFL stars Tom Brady and Von Miller, where Brady caught strays for his own derby look. "He looks like Jim Carey as Cuban Pete in The Mask!" a user commented. 

While NBC host Dylan Dreyer had a major wardrobe malfunction at the 145th running of the Kentucky Derby in 2019, it was not the first or last time she was criticized for her big race-day looks. At the 2025 Derby, she shared an Instagram post that showed off her messy look. "Not a whole lot more I can add to the earlier comments. Dylan your outfit AND hat was awful!! You are always wearing something nice and classy. Too much southern bourbon??? Lol," one user commented. Someone else was quick to point out how baggy and wrinkly the pink and green outfit was. "Love you and the way you usually look but you look kind of like a bag lady in this," someone pointed out. 

Unlike Dreyer's inappropriate on-air outfit that caused quite the stir, not all of her Derby outfits have been met with criticism. In fact, they are usually met with an outpouring of online praise. Her 2018 Kentucky Derby look was one of her best, where she wore an elegant navy-blue dress with colorful florals and a wide-brim hat that matched the dress flawlessly. The elaborate hat stole the show, garnering compliments on her Instagram post showing off the fashionable ensemble. "You look gorgeous!! Love watching your coverage today!! Great hat!!" a user commented. "You totally rock the Derby fashion! You're welcome here in Kentucky anytime!" a Kentucky local added.

As the popular news host continues to cover the prestigious horse race from Louisville, Kentucky, Dreyer's transformation is wild to see as her Derby fashion evolves. While she has made some bold and outlandish fashion choices, social media users continue to enjoy watching her sport multiple high-fashion Derby looks a year.