Dylan Dreyer’s fashion choices at the Kentucky Derby 2026 not only highlighted her unique style but also sparked playful banter with her TODAY Show co-stars, making her outfits a central talking point of the event.
This year, Dreyer wore five different dresses over the two days of the Derby, showcasing a range of styles that captivated viewers. Her first ensemble featured a green Lela Rose dress paired with a matching hat adorned with pink feathers. Following that, she donned a pink floral Eliza J dress complemented by a larger pink hat embellished with an oversized bow. Fans took to social media to praise her looks, with one calling her a “porcelain doll.”
That context matters because it reveals how Dylan has become synonymous with Derby fashion. Collaborating with milliner Christine A. Moore, she designed five custom hats for each dress, ensuring that every outfit was not just stylish but also uniquely hers. Notably, she often opts for brands like Eliza J and Vince Camuto for her Derby attire.
Interestingly, Dreyer involves her family in her fashion decisions—particularly her son Calvin, who is quite opinionated about her outfits. She humorously stated, “If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too.” This familial touch adds an endearing layer to her public persona.
During the coverage of the Derby, which spans approximately seven hours on air from 7 a.m. to 9 p.m., viewers witnessed not just fashion but also light-hearted exchanges among co-hosts. For instance, co-host Sheinelle Jones asked Dreyer about the hat box she had played with earlier—a moment that showcased their camaraderie.
Dreyer’s style choices have evolved over the years; last year’s memorable look included a green spaghetti strap dress featuring a floral print. However, this year’s array of outfits has set a new standard for what viewers can expect from her during future Derbies.
As observers look forward to upcoming events like the next Kentucky Derby in 2027, they anticipate whether Dreyer will continue to innovate with her fashion choices or perhaps introduce new elements into her wardrobe.