Dylan Dreyer made a striking impression at the Kentucky Derby 2026 with five different outfits, showcasing her unique style and family involvement in fashion.
Her first look featured a green Lela Rose dress complemented by a matching hat adorned with pink feathers. The second outfit was a pink floral Eliza J dress, paired with a larger pink hat embellished with an oversized bow.
Dreyer collaborated with milliner Christine A. Moore to design five custom hats for her dresses. She expressed her preference for brands like Eliza J and Vince Camuto, stating, “I really don’t like to get very expensive dresses.”
Her sons played an important role in her outfit selection process. Calvin, in particular, is known for being very opinionated about her choices. “If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too,” she noted.
Dylan wore nude Nine West heels during the broadcast but opted for purple Crocs when off-camera. Social media buzzed with praise for her outfits, with fans calling her a ‘porcelain doll’.
The Kentucky Derby coverage featuring Dreyer has become a must-watch tradition for TODAY Show audiences. Observers noted the playful banter between her and co-stars regarding her fashion choices.
As the event spanned two days, Dreyer spent approximately seven hours on air. Her notable dress from 2022—a green spaghetti strap dress with floral print—also drew attention this year.
