Dylan Dreyer wore five different dresses at the Kentucky Derby 2026, held at Churchill Downs in Louisville, Kentucky. Her outfits sparked playful banter with her TODAY Show co-stars while highlighting her unique style.
Dreyer’s first outfit featured a green Lela Rose dress paired with a matching hat adorned with pink feathers. She then changed into a pink floral Eliza J dress, complemented by a larger pink hat embellished with an oversized bow. Each outfit was designed to stand out during the prestigious event.
Dylan collaborated with milliner Christine A. Moore to create five custom hats for her dresses. Her favorite brands include Eliza J and Vince Camuto, which she favors for their stylish yet affordable options. “I really don’t like to get very expensive dresses,” she said.
Her sons played a significant role in her outfit selection, particularly son Calvin, who is known for his strong opinions on fashion choices. “If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too,” Dreyer explained.
On camera, she wore nude Nine West heels but opted for purple Crocs off-camera for comfort. Fans praised her outfits on social media, calling her a “porcelain doll” and expressing admiration for her style.
Dylan’s coverage of the Kentucky Derby has become a must-watch tradition for TODAY Show audiences over the years. She has been reporting on this event for over a decade, bringing excitement and personal flair to the broadcasts.
As she continues to evolve her fashion choices, observers can expect more creative outfits from Dreyer in future events. The next Derby promises to showcase even more fashion trends as it approaches its 153rd edition in 2027.
