Dylan Dreyer’s fashion choices at the Kentucky Derby 2026 sparked playful banter with her TODAY Show co-stars, showcasing her unique style and family involvement in outfit selection. At Churchill Downs in Louisville, Kentucky, she wore five different dresses over the two-day event.
Dylan’s first outfit featured a stunning green Lela Rose dress paired with a matching hat adorned with pink feathers. Her second look was equally captivating—a pink floral Eliza J dress complemented by a larger pink hat embellished with an oversized bow. Each ensemble reflected not only her taste but also the creative collaboration with milliner Christine A. Moore, who designed five custom hats for her dresses.
With a busy schedule on Derby day, Dylan spent seven hours on air, captivating fans who eagerly awaited her fashion reveals. “If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too,” she shared about her outfit selection process involving her three sons, particularly Calvin, who is quite opinionated.
Throughout the event, social media buzzed with compliments for Dylan’s outfits. One fan commented, “Dylan is looking stunning,” while others likened her to a “porcelain doll.” She also humorously revealed that while she wore nude Nine West heels on camera, she opted for purple Crocs off-camera—an amusing contrast to her glamorous looks.
Dylan has covered the Kentucky Derby for NBC for over a decade, and each year brings fresh excitement and anticipation among viewers. Her outfits have become integral to the tradition of Derby coverage that audiences look forward to.
Key outfits from Dylan Dreyer:
- Green Lela Rose dress with pink feathered hat
- Pink floral Eliza J dress with oversized bow hat
- Five custom hats designed by Christine A. Moore Millinery
As fans continue to celebrate Dylan’s fashion choices, the Kentucky Derby remains a highlight of the year for many. Observers anticipate what unique styles she will bring to future events as she prepares for another round of creative collaborations and family-influenced selections.
