After covering the Kentucky Derby for NBC for over a decade, Dylan Dreyer has a foolproof method for selecting outfits that honor her personal style and the pomp and circumstance of the annual event.
“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 tells TODAY.com.
Over the course of the two-day event, Dylan sports five different dresses, so she’s always conscious of her budget while she’s shopping.
“I really don’t like to get very expensive dresses,” she says, citing Eliza J and Vince Camuto as two of her go-to affordable brands.
Dylan tends to gravitate towards brands that have “girly” designs and “reasonable price points.” She’s also conscious of current fashion trends while selecting her Kentucky Derby wardrobe.
“This year, I know it’s a lot of florals. It’s a lot of appliqués. And there’s a fine line between a floral Derby dress and an Easter dress,” she says.
Dylan, a mother of three, often likes to get the seal of approval from her sons before finalizing her Derby looks.
“I will try on a lot of my dresses and Ollie, my middle guy, just thinks I look pretty in everything. 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,” she says.
Dylan’s 2026 Kentucky Derby Dresses and Hats
This year, Dylan has five fabulous frocks lined up for her Derby duties. For Friday morning, she selected a green Lela Rose dress.
On Friday afternoon, she changed into an Eliza J dress.
“It’s got all sorts of different colored pink flowers and a lot of sparkle,” she says.
On Saturday, Dylan will start the day wearing an Eliza J dress “with yellow flowers all over it.” In the afternoon, she’ll rock two different dresses.
“I have one for when I do red carpet interviews. That’s the Camilla dress. It’s a showstopper kind of dress. It’s a little different than what I’m used to wearing. It’s white with flowers. It’s got spaghetti straps. It’s a little shorter than what I wear, but it’s girly,” she says.
Next, she’ll slip into a strapless Eliza J dress.
“It’s a light sage green dress with lace overlay all over the whole thing, so that’s really pretty too,” she says.
Big and beautiful hats are always en vogue at the Kentucky Derby. For years, Dylan has worked with milliner Christine Moore to source one-of-a-kind hats that complement her camera-ready outfits. She first met Moore through TODAY’s Al Roker, who previously sported several Derby hats designed by the hat maker.
One of the five hats Dylan will wear over a two-day period. Christine A. Moore Millinery LLC
“I send her pictures of my dress. She gives me her opinions on which dresses she thinks would be best and what kind of hat she can make for it, and she designs the hats directly off the dresses I’m wearing.
This year, Moore has designed five custom hats for Dylan to wear with her five dresses. After the event, the milliner often asks Dylan to sign each hat, then donates them to different charity events. Sometimes, they even end up on display in the Kentucky Derby Museum.
The hats by Christine A. Moore Millinery are custom designed for each dress. Christine A. Moore Millinery LLC
When it comes to footwear, Dylan tends to pick a shoe that will go with all of her dresses. This year, she’ll be sporting a pair of nude Nine West heels while she’s on camera. But you’re more likely to find her in something a bit more comfier in between on-air spots and her red carpet duties, especially since she walks quite a bit throughout the day.
“If you actually saw me not on camera, it’s like a pair of Crocs or a pair of sandals, depending on what the weather’s going to be. I have these purple Crocs with fur on the inside. I will be wearing those most of the time because I’m literally on air from 7 a.m. until about 9 p.m. so it’s a long day to be in heels,” she says.
As a weather expert, Dylan knows you should always pack something for a potential cold snap, so she’s ready for the chilly mornings.
“It’s funny because in between hits, I’m wearing sweatpants and sweatshirts and my heated jacket. But when the camera’s on, I dress up and try to look the part,” she jokes.
Dylan’s Favorite Kentucky Derby Dress of All Time
Dylan has sported countless gorgeous dresses to the Kentucky Derby over the years, but one in particular stands out in her memory: a green spaghetti strap dress with a floral print.
In 2022, Dylan posted a photo of herself wearing the gown as she crouched in a bathroom stall at Churchill Downs and used a breast pump in between filming.
“I placed my bet on ‘Mama’s A Cow’ for the win,” she wrote in the caption. “Happy Mother’s Day to all the moms out there getting it done all day every day. Sometimes I don’t know how we do it but we do!”
Looking back on the dress, Dylan says it was “absolutely stunning and so different from what I would normally wear.” She’s also considering breaking it out once again for an upcoming special occasion.
“I might actually even wear that dress to Al Roker’s daughter’s wedding!” she says.
