The Most Inappropriate Outfits Jenna Bush Hager Has Ever Worn

Jenna Bush Hager is no stranger to the spotlight. She has not one, but two former U.S. presidents in the family, and grew up in the public eye as a first daughter during George W. Bush's presidency from 2001 to 2009. Though Jenna Bush Hager has had to deal with some tragedies, she is now a successful public figure in her own right, serving as a journalist and penning a NYT bestselling book based upon her time as an intern with UNICEF. As an accomplished news personality, the anchor gets plenty of air time with her latest gig as host of "Today With Jenna and Friends" on NBC's 10 a.m. morning time slot, generating lots of chatter on everything from her commentary to her outfits.

With the nation's eyes fixed on her every morning, Hager appears on television screens sporting a personal style full of both hits and misses, and it's not uncommon for the top comments on her social media to explicitly reveal how viewers felt about her daily wardrobe choice. From too-bright colors to in-your-face florals, the "Ana's Story: A Journey of Hope" author is known for her polarizing choices, which are not always seasonally appropriate. Here's a look at her biggest misses, which have taken center stage not only on her own show, but at public appearances and even at New York Fashion Week.

Jenna Bush Hager hit the event carpet at the CFDA Fashion Awards in June of 2019 wearing what can only be described as her homage to a big red tomato. While she did achieve a near-exact color match to the hue of the event's logo, that did nothing to keep her from sticking out like a sore thumb, and as someone who lives such a lavish lifestyle, we know she's capable of much better. Buried under a sea of shiny tiered fabric, the blood-red dress would've been more at home as the centerpiece of a fashion crime scene, and not even Hager's sleek silver heels could save the look.

Although the tent-like cut of the garment was likely due to the fact that the popular morning show host was pregnant with her third child at the time, she could have chosen something with a bit more shape. Being completely swallowed by the dress did her no favors, and we're pleased to report that we haven't seen the television personality wear anything that overwhelms her frame in such a massive way since this major misstep.

We know that Jenna Bush Hager understands the idea that sometimes less is more after seeing her stunning makeup-free moments, but unfortunately that concept didn't extend to the floral disaster she wore on the "Today" show in September of 2023. The matching tank and cropped pants set had decent bones with a neutral black background, and it could've been a sleek choice for the first few days of a warmer fall, but an overwhelming print ruined the balance of the outfit. The tiled pattern quickly caused chaos for the eye, with each square featuring flowers of all colors, shapes, and sizes, making the overall effect much too busy.

Perhaps Hager should've taken a cue from her (now former) co-host Hoda Kotb when she also chose a sleeveless look, but pulled it off with more finesse than her on-air counterpart. Kotb kept her 'fit to one dark wine-colored hue, with floor-length trousers that didn't cut her legs off at the ankle like Hager's crops. The high neck of her tank top completed the chic aesthetic, making her the more fashionable host of the day.

Generally people want to look fashionable when attending one of the biggest events in the fashion industry, especially anything associated with the famed New York Fashion Week, but Jenna Bush Hager had other ideas. Hager opted for a interesting look at the Sergio Hudson show in February of 2024. 

Although Jenna Bush Hager has had a stunning transformation throughout the years, the Texas native is still prone to some misses, and her appearance at fashion week unfortunately fell into this category. Hager's gold dress sported full sheer sleeves and a long skirt, which mixed elements of the sheer fabric with what appeared to be pleated satin. The top required a dark camisole due to the open drape of the neckline, and the look was topped off with a wide shiny belt. The television producer chose to forego her typical chunky necklaces, which is the only positive thing we can say about this molten metal disaster. Even the color photographed as more of a drab tan than a true gold, making a dull presentation out of what should have been an opportunity for Hager to show off her style.

Everyone remembers when "Barbie" had her moment during the summer of 2023, and it seems like she made quite an impression on Jenna Bush Hager. In what could possibly be one of her more bizarre outfit choices to date, the morning show host chose to wear a pink mini-suit that would have better suited the fictional character during a trip to The Empire State Building in April of 2024.

While the bubblegum color was seasonally appropriate for spring, the skirt of the suit hung questionably short, and Hager chose to sport it with bare legs and a pair of slouchy knee-high off-white boots that totally threw the balance of the 'fit. While there's nothing wrong with showing a little skin, which Hager continued to do later in the year on a moms' night out, the height of the ivory boots paired with the thigh-skimming hemline left us feeling like a sleeker heel in a darker color would've been a better choice for footwear. We do love to see the "Sisters First" author in fun colors instead of the boring black ensembles she occasionally gravitates to, so we're hoping she doesn't give up on attempting to rock the pastels — she just needs a bit of styling help.

If we had to list Jenna Bush Hager's most frequent fashion faux pas, we'd have to say that it's her habit for dressing out of season. While she's been known to sport sleeveless looks and short skirts with bare legs well into fall, the outfit she wore on the "Today" show when Ciara appeared on January 29, 2024 had fans really scratching their heads. While the black dress was chic, the spaghetti straps were a bizarre choice for January, and the lace detailing seemed out of place at 10 in the morning.

One top commenter on Instagram wrote, "Jenna please get a new person to pick out your clothing. It's winter so dress like it is. Save the sleeveless for summer. Your cohost [sic] are wearing furs and long sleeves and you are wearing the opposite." Another user chimed in with some helpful tips, advising, "Jenna's dress is so gorgeous but really for the morning show attire and for the season, being that it's winter, it would have been so chic and cute with an oversized blazer and a nice juxtapose to her dress." Here's hoping Hager takes a cue from her audience and thinks more about dressing for the weather.