5 Outdated Outfits Jill Biden Was Caught Wearing

Over the years, many first ladies have been widely acclaimed for their impeccable style. Jackie Kennedy, Nancy Reagan, Melania Trump, and Michelle Obama are obvious modern examples, but back in the day, Dolley Madison, Julia Tyler, and Angelica Van Buren were no slouches in the fashion department themselves. On the other end of the spectrum, Jill Biden didn't come to the White House to be a style icon. Dr. Biden is a teacher first and foremost, so she hasn't had the privilege of jetting to Milan for Fashion Week or curating a wardrobe full of bespoke gowns. She tends to prefer simple suits and comfortable dresses that would easily work as well in the classroom as in a White House luncheon. 

By favoring American designers such as Calvin Klein, Christian Soriano, and Tom Ford, the former first lady literally wore her patriotism on her sleeve. That's not to say that Biden hasn't had her style missteps, however. During her husband's tenure there were a number of occasions where her chosen outfits came off as a bit, well, behind the times. True, a woman of a certain age may not be as concerned about being fashion-forward as an average Gen Z-er, but on the other hand, Dame Helen Mirren and fellow Oscar winner Meryl Streep might have a word or two to say about that. As such, in the interests of fairness, here's an apologetic roundup of the former first lady's most outdated looks.

Speaking before an approving crowd at the Clinton Global Initiative, Jill Biden proudly announced her husband's administration would provide half a billion dollars in funding for women's health research. The first lady stunned in an all-pink ensemble — right down to the pink and silver heels — that would have gotten high marks from Barbie herself. There was just one problem: This event took place in Fall 2024, more than a year after the release of the blockbuster Margot Robbie movie. If you recall, there was no escaping Barbiecore, including at the Golden Globes and other major entertainment events. Biden would have been right in step with the times had she been in the pink back then, but this belated nod to the iconic doll just seemed as though she was showing off a trend that had already been stowed away in the attic of Barbie's Dream House.

Dr. Jill Biden has obviously had a stunning transformation over the years, but just like everybody else, not every look suits her. In support of the U.S. Postal Service in 2020, the first lady encouraged Americans to post a letter, old-school style. Maybe she was feeling a bit old-school nostalgic herself when Biden selected this dress for the accompanying promotional photograph. The empire waist and flowing sleeves could have come straight from the 1970s, when boho style was all the rage. Flowy fabrics and loose fits represented freedom from the constraints of traditional authority (or the Establishment) and the embrace of environmentalism and natural living. If the dress were a paisley print and Biden had added a few long, beaded necklaces, it would have been a perfect nod to the era. But this was during the height of the COVID-19 pandemic, when people were living in their sweatpants and buying funky masks on Etsy. Whatever her intent, the retro look didn't fly.

All due respect to Jill Biden for having the figure to pull off skinny jeans in the first place, and for having the confidence to rock them as the first lady of the United States no less. She was youthfully chic here in 2016, in these form-fitting pants and a striped blazer, which added a touch of class as she delivered a speech at the closing ceremony of the Invictus Games (the biennial international sports event, open to injured and disabled veterans, was created by none other than Prince Harry himself back in 2014.) By this time, though, the super-slim denim trend had already begun to give way to a more relaxed silhouette. Once again, the former first lady looked as though she were trying to catch up with the current fashion trend before it became obsolete — and didn't quite make it in time.

Variations of the shirtwaist dress have been around for more than a century, as women's clothes subtly took on a more masculine edge. The look, typically featuring a collared button-down top and cinched waist, is most often associated with the 1910s, 40s, 50s, and 80s, but it's been enjoying a bit of a comeback lately. When Jill Biden isn't wearing suits, you'll often see her in some style of the shirtdress, as in this picture from August 2023 when she visited a D.C. middle school on their first day back in class. What makes the dress look dated isn't the cut, but the pattern. It's giving off major "Minecraft" vibes (the super popular video game that's been around since 2009). The young teens who met the first lady may have felt a sweet jolt of nostalgia at seeing her blocky dress, but most of them were probably too busy creating TikToks to craft swords, fight zombies, and trade with piglins anymore.

The babydoll dress — a loose, above-the-knee style closely resembling lingerie — initially gained popularity in the 1940s and the ultra girly style continued to evolve over the next two decades. Blending innocence with sexiness, it symbolized the emergence of greater bodily autonomy, freedoms, and opportunities for women and, nowadays, is favored by the likes of Sabrina Carpenter who wears one while performing sultry hits like "Espresso." Jill Biden clearly couldn't resist its charms either, posing for the above pic in August 2022 alongside her beloved husband. Unfortunately, this time she was a little ahead of the game. Babydolls enjoyed a comeback a year later, thanks in part to the popularity of "M3GAN" and the creepy robot doll whose cute dress belied her evil nature (really). Plus, the look was just a little too plain and twee for a first lady who spent most of her days in colorful suit sets.