Dylan Dreyer’s fashion choices at the Kentucky Derby 2026 sparked playful banter among her TODAY Show co-stars while showcasing her unique style. At Churchill Downs in Louisville, Kentucky, she wore five different dresses throughout the event.
Key outfits:
- Dylan’s first outfit featured a green Lela Rose dress paired with a green hat adorned with pink feathers.
- Her second outfit was a pink floral Eliza J dress complemented by a larger pink hat embellished with an oversized bow.
- Each dress was designed to match a custom hat created in collaboration with milliner Christine A. Moore.
Dylan’s favorite brands—Eliza J and Vince Camuto—helped define her Derby look. Interestingly, her sons, particularly Calvin, played a significant role in selecting her outfits. “If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too,” she said, emphasizing the family involvement in her fashion decisions.
Fans took to social media to express their admiration for Dylan’s style, calling her a “porcelain doll.” This kind of praise is not new; her outfits have consistently drawn positive attention over the years. In fact, Dylan has covered the Kentucky Derby for NBC for over a decade now, making her attire a focal point of the event.
Fashion highlights:
- Dylan wore nude Nine West heels on camera but opted for purple Crocs off-camera—a testament to comfort amidst glamour.
- Her notable dress from 2022—a green spaghetti strap dress with floral print—also received acclaim.
- This year’s coverage saw Dylan on air for seven hours across two days, making her presence felt throughout the festivities.
The playful interactions between Dylan and her co-stars added another layer of enjoyment for viewers. As Sheinelle Jones quipped during one broadcast, “What kind of hat box did you play with?” Such moments highlight not just the fashion but also the camaraderie that makes watching the Derby so engaging.
As anticipation builds for future events, including next year’s Kentucky Derby, fans will undoubtedly look forward to seeing how Dylan continues to blend family input with high-fashion choices—a trend that keeps evolving year after year.
