Jenna Bush Hager’s Remarkable Style Evolution

At 17 years old in the early 2000s, Jenna Bush Hager’s style was that of many teens and young adults, but with a preppy twist. She was seen wearing flared jeans or pants, relaxed T-shirts, and the lacy wraparound tops that were popular then. During the first inaugural ball for her father George W. Bush, Bush Hager opted for a pretty floral strapless black dress that almost caused an embarrassing moment, as she later revealed on “Watch What Happens Live with Andy Cohen.” Looking at her father-daughter dance and gesturing to her chest, she shared, “It’s really sweet, but if you notice my hand is going like this, my dress fell off.”

George W. Bush’s daughter may have gotten into some trouble while he was POTUS, such as getting caught drinking underage, but she matured over the years, along with her fashion sense. When Jenna Bush Hager got married to Henry Hager in 2008 (which later raised a few red flags), she chose an elegant embroidered Oscar de la Renta dress and had her hair in loose waves. On having her wedding at the White House, Bush Hager told Vogue (via NBC News), “There’s a glamour to it, I know. But Henry and I are far less glamorous than the White House.” Bush’s style does indeed reflect her low-key, yet fun nature, and since branching off on her own as a married woman, she has found her own unique sense of style.

As Jenna Bush Hager went from teaching elementary school to becoming a correspondent for “Today,” she became more comfortable in the spotlight, and her style went from Y2K party glam to a more refined look. Bush Hager often accompanied her family to important events, such as her mom Laura Bush’s book signing for “Spoken from the Heart” in May 2010, where she styled her T-shirt to look polished and sophisticated as she greeted fans.

Over the years, Bush Hager continued to be influential with her philanthropic efforts since she first worked with UNICEF in 2006. Aside from working with the organization, the former teacher helped drum up $180,000 in 2013 for the Houston-based charity Small Steps Nurturing Center, per Culture Map Houston. As the co-chair, she wore a bright yellow-and-green striped dress that was perfect for the daytime luncheon, and she kept her makeup light with just a touch of blush. Elsewhere that year, Bush Hager looked much more glam in a cobalt-blue gown with a plunging neckline for the 2013 UNICEF Snowflake Ball. The new mom of first daughter Mila completed the outfit with a small glittery handbag and looked simply gorgeous with her hair in a loose updo that showed off her dangly earrings.

Jenna Bush Hager’s star continued to rise as she cemented herself in the celebrity world with fabulous invitations to upscale events. In 2014, she hobnobbed with Hollywood’s famous faces, such as Andrew Garfield and George Lopez, at the GQ Gentleman’s Ball. Bush Hager wore the perfect LBD with sheer paneling along the chest and back that was decorated with crystal embellishments. The rest of her look was simple, with just her wedding ring and a pair of stud earrings. Bush Hager wowed yet again at her first-ever Golden Globes appearance in 2017 in an emerald-green off-the-shoulder gown that landed her on a few best-dressed lists. The floor-length dress needed no other accessories than a few pieces of jewelry, which included turquoise earrings.

Bush Hager switched up her style from classic to avant-garde at another one of her firsts — the 2018 Met Gala as a guest instead of a correspondent. This time, she wore a bright-red lace gown that looked like it was made out of rose petals. The Lela Rose creation was perfect for that year’s “Heavenly Bodies: Fashion and the Catholic Imagination” theme, and it was unlike anything we’ve seen her in. While it wasn’t one of the most stunning Met Gala looks ever, Bush Hager’s dress that night was certainly one of the best she’s ever worn.

What better way to show up at the CFDA Fashion Awards than with a big red cape dress? Jenna Bush Hager did exactly that in 2019 with her Lela Rose frock that hid an adorable detail. “I feel great because I’m hiding a large baby under here,” she told Access Hollywood. “I think that’s the thing about Lela, she creates clothes that women want to wear and that they feel good in. And at an event like this, you want to feel good.”

While Bush Hager never shied away from color, she began gravitating toward brighter hues, as she showed while at the Empire State Building in April 2024. Wearing a three-piece bubblegum-pink jacket and skirt set with a vest, the mom-of-three looked like a fun and flirty girl boss. Bush Hager was there to light up the tower in pink and purple to celebrate her and Hoda Kotb’s fifth year with “Today,” and we have to say, she definitely looked pretty in pink.

After Hoda Kotb announced her departure from “Today” in September 2024, Jenna Bush Hager began her daytime talk-show career solo the following January, starring on “Today with Jenna and Friends.” The anchor regularly shows off her revolving ‘fits while on-air, which include smart black sheaths and fitted jackets. Bush Hager doesn’t always get it right, however. On February 5, during “Jenna’s Morning Boost” segment on “Today,” she wore a black-and-white jacket and pants combo that featured bold paisley prints. “Earlier, all the boys on the show said I look like a pack of cards,” she laughed later on “Today with Jenna and Friends.”

Still, Bush Hager continues to knock it out of the park with her many looks, which she shared in an Instagram reel of her past episodes. From chic maxi skirts to satin sets to the cozy blue-and-white striped cardigan she wore on a May episode of “Today with Jenna and Friends,” the avid reader never runs out of fun looks. As she continues to rule morning television, fans are sure to see more of her ever-changing style, and we know Bush Hager will have the most fun while being her own stylist.