Dylan Dreyer turned heads at the Kentucky Derby 2026, showcasing five distinct outfits that sparked playful banter among her TODAY Show co-stars. Each dress not only highlighted her unique style but also featured input from her family, especially her fashion-savvy son Calvin.
Her first look was a vibrant green Lela Rose dress paired with a matching hat adorned with pink feathers. The ensemble set a lively tone for the day. Next up was a pink floral Eliza J dress, complete with an oversized pink hat that made a statement all on its own. Fans on social media were quick to comment, dubbing her a “porcelain doll” for her stunning looks.
But it wasn’t just about the dresses. Dylan collaborated with the talented milliner Christine A. Moore to design five custom hats—one for each outfit. This creative partnership added an extra layer of flair to her looks, aligning perfectly with the festive atmosphere of Churchill Downs.
Key elements of Dylan’s Kentucky Derby fashion:
- Dylan wore five different dresses throughout the event, showcasing her versatility.
- Her favorite brands included Eliza J and Vince Camuto, known for their elegant styles.
- Calvin, her son, played a significant role in choosing her outfits—”If Calvin doesn’t like it, I’m not wearing it,” she said.
On camera, she opted for nude Nine West heels, but off-camera? She slipped into comfortable purple Crocs—a perfect example of balancing style and practicality during long hours on air.
Dylan has been covering the Kentucky Derby for NBC for over a decade now—and each year brings its own excitement. This year’s coverage spanned nine hours from 7 a.m. to 9 p.m., making it a must-watch tradition for fans.
The playful exchanges with co-stars like Sheinelle Jones added to the fun atmosphere. “What kind of hat box did you play with?” Jones teased, highlighting the lighthearted spirit that permeated their coverage.
As anticipation builds for next year’s event, observers are eager to see how Dylan will top this year’s fashionable displays. With her unique sense of style and family involvement in outfit selection, one thing is certain: she’ll continue to dazzle at future Derbys.