Dylan Dreyer's Trendiest Denim Looks Prove She Can Keep It Casual & Still Stay Chic

The "Today" show's Dylan Dreyer has had a stunning transformation since joining the program in 2012. And while she is known to dress up — and wear gorgeous outfits to the Kentucky Derby — she also knows how to rock a fabulous denim look. From baggy jeans to jean jackets, and the fact that Dreyer hasn't given up skinny jeans, we can take some major style inspiration from Dreyer's best denim looks over the years.

In a September 2016 pregnancy diary for "Today," when Dreyer was pregnant with her firstborn son Calvin with ex Brian Fichera, she shared her strategy for choosing her work wardrobe. "I don't have a stylist ... everything you see me wear on TV I've purchased, and I don't like to spend a lot of money on clothes because I don't like to repeat all that much," she explained. Dreyer added that she is hurt when fans share negative commentary on her style " ... because I'm trying my best here."

Over the years, Dreyer seems to have gotten more confident in her choices. In a May 2026 interview with the "Today" website, Dreyer explained her mindset for picking her Kentucky Derby outfits, which may extend to her day-to-day professional fashion as well: "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." One of her wardrobe staples seems to be denim, which she has worn on red carpets and while filming. And any attempts to look "on trend" and "cool" are often successful when she steps out in the beloved fabric.

Wearing denim-on-denim is one of those '90s trends that we are happy is back today, and Dylan Dreyer's version of this style was fabulous. In a photo taken on January 8, 2026, as she was leaving the "Today" show, Dreyer wore a light-wash jean jacket with a cozy white lining. She paired this with a white sweater and a pair of oversized, medium-wash jeans over boots. Dreyer looked warm on the winter day and totally stylish at the same time.

Jeans on the red carpet has never looked so good! Dylan Dreyer wore a medium-wash, high-waisted pair of jeans while hosting the SiriusXM "Today Show Radio" special on June 10, 2025. She dressed up the jeans with a white blouse and a dainty necklace, elevated even further with light tan heels. Although denim isn't a typical red-carpet choice, in this picture from the event, Dreyer looked beautiful and made the whole outfit fit right in. 

Who knew a jean skirt could look pretty and professional? Dylan Dreyer proved that in this outfit from Hoda Kotb's Joy 101 Launch Event on May 28, 2025. She wore a long denim skirt with a high slit up the middle and a frayed hem, which she paired with a white belt and light tan heels. Her pink-and-white striped collared shirt was a bright pop of color, and her dangly white earrings tied the whole outfit together. This is the blueprint on how to upscale denim.

When Dylan Dreyer traveled to Springfield, Missouri, with "Today" co-stars Al Roker and Laura Jarrett, she was on trend in a pair of baggy jeans with sneakers and a white, button-up sweater vest. In this picture, posted to Instagram on April 29, 2026, she looks so stylish yet laidback in this spring outfit with the sun shining on her. Dreyer's blond hair was parted down the middle and pulled away from her face, and she looked genuinely happy in front of a yellow convertible with Roker and Jarrett. 

Dylan Dreyer proved skinny jeans are still cool when she covered the 2026 Winter Olympics for "Today." She shared a photo of one of her cute outfits on Instagram on February 13, 2026, where she proudly rocked dark skinny jeans with winter boots and a Polo Ralph Lauren-designed Olympics cardigan. The zip-up sweater had the American flag and Olympic rings on the back. "One of the best parts about the Olympics is the swag!" she captioned the post in part.

Dylan Dreyer was the perfect mix of chic and casual in this outfit. She paired a black dress with a light-wash denim jacket while filming "Today" with co-star Craig Melvin on September 1, 2023. The jean jacket helped dress-down the more formal black dress, but it still looked stylish and professional. Dryer accessorized her outfit with several shiny rings and a bracelet. The whole look was tied together with a pink manicure and matching pink lipstick.