‘Today’s Dylan Dreyer Shows Off Her 2026 Kentucky Derby Outfits

Dylan Dreyer followed up the third hour of Today crew’s Route 66 trip by traveling to another major event.

The Today meteorologist continued her annual tradition of covering the Kentucky Derby for Today and NBC Sports. Like the rest of the event’s attendees, Dreyer sported several stylish looks to watch the races at the Churchill Downs Racetrack in Louisville, Kentucky.

“Kentucky Derby look #1…just a pop of pink for the Kentucky Oaks!” she captioned Instagram photos of her first outfit on Friday, May 1. “I love being here with some of my favorite people! @miketiriconbc @getrusso_ @makeupby_vadee (Dress: @lelarose Hat: @camhatsnyc).”

As her caption noted, Dreyer wore a matching green dress and hat, the latter adorned with a pink feather. She wore the outfit while reporting live from Kentucky on Friday’s episode of Today, during which she and NBC Sports’ Mike Tirico toasted to Dreyer and Craig Melvin‘s new Today podcasts, The Parent Chat and Glass Half Full.

Later on Friday, Dreyer swapped the green for a floral pink dress and elaborate bow hat. “Look #2. An amazing day at the Kentucky Oaks with amazing people!! Dress: @elizajdresses Hat: @camhatsnyc Hair: @getrusso_ Makeup: @makeupby_vadee,” she captioned more Kentucky Derby Instagram pics, including several of herself posing with other attendees dressed in pink.

 

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In a funny behind-the-scenes Instagram clip, Dreyer eventually ditched her nude heels for a pair of purple Crocs. “Heels are nice and all but I can’t get out of them fast enough!!” she jokingly captioned the Friday Instagram post.

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For her first look on Saturday, May 2, Dreyer channeled the sunny weather by wearing a yellow floral ensemble. “Look #3 from @todayshow this morning!” she captioned another Instagram upload. “And a huge thank you to my milliner (omg! I have a milliner!) for more than a decade, the incredible @camhatsnyc for joining us so early on such a busy Derby day!! Dress: @elizajdresses Hat: @camhatsnyc Hair: @getrusso_ Makeup: @makeupby_vadee.”

Dreyer appeared on Saturday’s episode of Weekend Today to share which horses were favored to win and to break down derby fashion with hat designer Christine Moore. “I love the movement to it,” Dreyer told Moore of her yellow hat.

Dreyer later walked the red carpet in a white floral minidress, which she paired with a blue hat featuring a pink bow and yellow feathers. “Look #4: Definitely didn’t dress for the weather but I loved this @camillawithlove from @rodeslouisville so much I had to wear it!” she captioned more Instagram pics on Saturday.

Dreyer concluded her time at the 2026 Kentucky Derby in a mint green strapless gown and matching hat. “Thanks to @makeupby_vadee for documenting this Derby of a day!!” she captioned an Instagram video showcasing her day at the Derby. “From sunrise to sunset…and I loved every minute of it surrounded by the best people!”

@todayshowanother kentucky derby in the books! 🤩💐👒🐎♬ original sound – TODAY Show

Dreyer broke down her Kentucky Derby fashion decisions in an interview with Today.com published on Saturday. “I try to be on trend, I try to be cool, I try to be fashionable. But I also like my standby brands that always work for me,” she shared. “I really don’t like to get very expensive dresses.”

Dreyer noted she tries to balance “girly” designs with “reasonable price points.” She also revealed that she tries on her looks ahead of time for her three sons — Calvin, Oliver, and Rusty. “I will try on a lot of my dresses and Ollie, my middle guy, just thinks I look pretty in everything,” she gushed. “But Calvin is very opinionated, and he’ll be like, ‘No, you can’t wear that. Nope, I don’t like it.’ Or, ‘Yes, that’s pretty.’ If Calvin doesn’t like it, I’m not wearing it because if he doesn’t like it, someone else won’t too.”

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