Dylan Dreyer's Best Fashion Moments Are An Ode To Her Playful Style

It is safe to say that Dylan Dreyer is a fashionista in her own right. As an NBC meteorologist and host who is most known for the "Today" show, Dreyer has plenty of opportunities to dress up for the camera. This is especially true when she covers the annual Kentucky Derby every May for NBC, which results in her pulling together five high-fashion looks each year. The hallmarks of her playful style include a strong blend of florals, bright colors, and fancy hats. 

Whether it is the Kentucky Derby or Halloween, Dreyer goes all out when she wants to dress up. As a TV personality who was born for the spotlight, she makes elaborate ensembles look natural and effortless. It is evident that she genuinely enjoys fashion and posing for the camera, and her bright smile elevates all of her unique looks. Unlike these times NBC's Dylan Dreyer's killer legs couldn't save her awful outfits, the star completely rocked these playful looks throughout the years. 

Dylan Dreyer regularly hosts and covers the annual Kentucky Derby for NBC's "Today." Given her longstanding tradition of attending the most exciting two minutes in sports, she tends to save some of her best and most playful looks for the swanky event at Churchill Downs in Louisville, Kentucky. On May 5, 2018, Dreyer wore one of her most iconic looks to date on the Derby red carpet: a sleeveless floral dress that elegantly flowed down into a small train. She paired the look with a subtle yet classy nude heel, completing her ensemble with a wide-brim hat that matched the colors of the dress beautifully. 

If there is one thing that is consistent across many of Dylan Dreyer's outfits, it is florals. The TV personality can often be spotted rocking a flowery look, whether it is at the Kentucky Derby or spring events around New York City. When she arrived at the Hudson River Park Friends 8th Annual Playground Committee Luncheon on March 08, 2024, in NYC, she was wearing a pink floral dress and purple heels that suited her usual style. The outfit just so happened to match the pink carpet flawlessly as an added bonus. 

Given Dylan Dreyer's long-standing tradition of attending at the Kentucky Derby, she knows a thing or two about rocking fancy and large hats. Every year, she covers the horse racing event with an array of looks that are seamlessly paired with elegant hats that match the rest of her ensembles beautifully. In 2022, she wore a deep green dress with bright florals that really popped out of the fabric. 

"This could be my most favorite Derby dress and hat!! It got the @zannarassi seal of approval! Many of you have been asking...the dress is @elizajdresses and the hat was a custom made by the incredible @camhatsnyc Thank you for making me feel fancy!!" Dreyer shared on Instagram. 

As one of the news anchors with the most inappropriate wardrobes, Dylan Dreyer is not shy about showing off her killer legs. At the 2026 Kentucky Derby, she arrived on the red carpet in a short floral sundress and a large colorful hat that stole the show. "Look #4: Definitely didn't dress for the weather but I loved this @camillawithlove from @rodeslouisville so much I had to wear it!" she posted on Instagram. Her fans loved the playful look that screamed springtime. "Gorgeous! You look stunning. I love your dress! It's perfect for you. That hat is a winner!" one user commented. 

It is no secret that Dylan Dreyer and her costars like to go all out for Halloween. For the Halloween-themed show for "Today" on October 31, 2023, in New York City, she arrived dressed as Pink. She even gave an epic lip-sync performance to the musician's hit song "Raise Your Glass" on the "Today" show. 

"Pretty sure I want to be Pink in my next life...I had too much fun!" she wrote on her Instagram. The one piece and shoelaced heels paired with the fake leg tattoo really highlighted her toned legs. "You kicked butt!!!! Girl you're In Shape!!!!!" a fan raved in the comment section. Despite it being a costume, it ultimately became one of the host's best fashion moments. 

Another Halloween costume ended up being one of Dylan Dreyer's most playful fashion moments. For Halloween day in 2016, she went on NBC's "Today" dressed like a Spice Girl. She wore a large platinum blond wig, a fluffy white coat, and carried a giant red lollipop to transform into Emma Bunton, aka Baby Spice. Her costars also dressed up for the holiday in New York City, with Tamron Hall as Uma Thurman's "Pulp Fiction" character, Mia Wallace, and Al Roker as Steve Urkel. The show fully embraced a '90s-themed Halloween that year, and Dreyer was not going to disappoint. 

Dylan Dreyer always makes sure to dress her best when enjoying airtime with her many famous costars on NBC's "Today." In 2024, she enjoyed onscreen mint juleps with Mike Tirico at the 150th Kentucky Derby. Given the special anniversary of the famous horse race, she made sure to dress to impress for the historic occasion.

She wore a black dress patterned with green and pink florals and a matching pink and black hat to top it off. "Dylan your dress & hat are so pretty! You look fantastic!" a user commented on their Instagram post from the coverage. "Love Dylan... her style and what she brings to NBC," another fan added. 

Dylan Dreyer always looks pretty in pink, which is likely why it is one of the most common colors she can be spotted in. For another 2024 look at the 150th running of the Kentucky Derby, she opted for an all-pink ensemble at The Longines Kentucky Oaks. 

The ensemble's color became even more fitting when she posed on the pink carpet. The playful style made her look like a TV-hosting Barbie. "Love all your looks but the pink is my fav!!" a user commented on her Instagram post. "Gorgeous! Beautiful color on you!" said another fan of the pink.

Dylan Dreyer isn't afraid of getting creative with her hairstyles either. At the 2024 People's Choice Country Awards held at the Grand Ole Opry in Nashville, Tennessee, she sported hair extensions that formed a beautiful long ponytail with several loops and braids. She seemed to have had plenty of fun experimenting with a different look that evening. "'Man, I feel like a woman' – Shania Twain Being on stage at @opry and presenting at the @peopleschoice Country Awards was a magical experience. I got to play dress up and do something even more special than usual. What a night!!" she raved on Instagram. "Absolutely rocking the whole country look," one fan assured her. 

Unlike Dylan Dreyer's 2019 Kentucky Derby look, which was a total hot mess, her 2025 red carpet dress matched her hat perfectly. She opted for an ensemble that was absolutely bursting with color wherever you looked, with a flurry of red, blue, green, pink, and yellow. The outfit was a testament to her usual colorful style that makes it hard for fans to predict what she will wear next. 

She made sure to give credit where credit was due for putting together the whole look. "Hung out with some pretty awesome people and did quite a bit in Look #4! Dress: @shopshoshanna from @shopgusmayer Hat: @camhatsnyc Hair: @getrusso_," she captioned her Instagram post.