Jill Biden's Biggest Fashion Fails Yet

Former former first lady Jill Biden rarely shared her thoughts on fashion during her time in the White House. Though she had a front-row seat to Michelle Obama facing scrutiny over her style during Barack Obama and Joe Biden's eight-year tenure as president and vice-president, respectively, she seemingly wasn't prepared for the level of attention her own looks would receive once she became first lady. After being told by Vogue in 2021 that there was an Instagram account dedicated solely to what she wore, Jill told the magazine: "It's kind of surprising, I think, how much commentary is made about what I wear or if I put my hair in a scrunchie. ... It's amazing how much people pay attention to every little detail."

However, like many other first ladies, Jill used the fact that people were paying attention to her sartorial choices to good advantage. She used her outfits to send a message and promoted the work of various American designers and labels all while serving one iconic fashion moment after another. In fact, she hit the ground running when it came to stellar first lady fashion, showing two of her best looks during her husband's 2021 inauguration: a blue dress and matching overcoat by Alexandra O'Neill and an ivory silk wool dress and cashmere coat by Gabriela Hearst. "I knew that my clothes could help me say something important," Jill said in 2023 after donating both ensembles to the Smithsonian's First Ladies Collection, according to The New York Times. She concluded her tenure as first lady with a bang as well when she donned a gorgeous purple Ralph Lauren coat and dress for Donald Trump's inauguration in January 2025.

However, not all of Jill's style choices have worked out. Some of her outfits divided the internet, while others ended up being deemed inappropriate. Here's a look at the former first lady's biggest fashion fails so far.

Despite having been married to a high-profile man for over four decades, Dr. Jill Biden maintained a relatively low profile for most of Joe Biden's political career due to her desire to keep her identity as an educator separate from her other role as a politician's wife. This became a bigger challenge when her husband became vice president, and she had to be accompanied by Secret Service agents 24/7, including to the school where she taught, Northern Virginia Community College. Still, she succeeded by avoiding drawing attention to her last name and marriage to Joe and having her security detail switch from suits to outfits her students would wear.

Jill couldn't avoid the spotlight when she was doing second lady duties, but she still seemingly tried to keep it low-key, at least fashion-wise. While she used her platform to spread awareness for the causes important to her, such as girls' education, she rarely took fashion risks, typically gravitating toward the same silhouettes in the eight years her husband was vice president: pencil dresses, skirt suits, coats, and the reliable blazer-and-dress combo. But in January 2015, Dr. Biden made a bold choice and chose a sleeveless green dress with an unusual floral design for her appearance at the inaugural Lincoln Awards at the John F. Kennedy Center in Washington, D.C. The rich green color looked stunning on the then-second lady, and her hair, makeup, jewelry, and shoes were on point, but it was impossible not to be distracted by what looked like a bunch of sea urchins stuck on the bottom half of her dress, turning what would have otherwise been a simple, elegant dress into a bizarre look.

In addition to being a mother and grandmother, Dr. Jill Biden's job as an English professor meant she was always around young people and was constantly exposed to their ideas, lingo, fashion, problems, and more. She had been praised for continuing to teach throughout her stint as second lady (and later first lady), with one of her former students telling The Washington Post in 2021: "Being that she interacts with normal people on a regular basis — because she is a teacher — I think that gives her a connection with citizens, especially people in my age group, people that go to college. I have comfort knowing that someone of influence is still involved."

It's unclear if Biden ever took fashion advice from her students, but perhaps she should have before deciding to put on this shiny, shimmering pink dress back in May 2011. She donned the above-the-knee frock, along with floral heels and a statement necklace, for a Mother's Day event she and then-first lady Michelle Obama hosted for mothers, grandmothers, and spouses of military men and women. Unfortunately, the dress gave "mom chaperoning her teen's prom" rather than "second lady leading a White House event." While it wasn't a somber gathering, her bright outfit seemed out of tune with the speech she gave about the difficulties faced by female servicemembers during that event. It didn't help that Biden didn't match the vibe of Obama, who wore a neutral gray midi dress.

Dr. Jill Biden may have been a little too late in hopping on the skinny jeans and blazer combo bandwagon that peaked in the early 2000s. In May 2016, the then-second lady gave a speech at the closing ceremony of the Invictus Games — a Paralympic-style sporting event for sick, wounded, and injured service personnel and veterans that was founded by Prince Harry — wearing a black-and-white pinstripe blazer, white top, skinny jeans, and a pair of yellow wedges. While the color palette matched the competition's signature colors of black and yellow, the overall look was giving business casual Beetlejuice going to the club with the girls after office hours.

The outfit was a step down from her more stylish looks earlier on in the tournament. Just a day before the closing ceremony of the Invictus Games, which was held in Florida that year, Dr. Biden showed up at the event's wheelchair rugby finals with then-Vice President Joe Biden wearing a much better iteration of the mismatched blazer-and-pants style. She rocked a light blue blazer over a dark V-neck top, paired with black ankle-length cigarette pants and matching loafers. Photos from the Games showed her looking effortlessly chic in the timeless look as she cheered on the competitors beside her husband and Prince Harry, with whom she had apparently struck a friendship. "Jill went to London for the last [Invictus] Games [in 2014] and she spent too much damn time with Prince Harry," Vice President Biden joked at the event, according to ABC News.

It's no secret that Dr. Jill Biden loves florals. In fact, they have been some of her best looks of all time, from the red gown she wore to the 2016 USO Gala to her $5,690 Oscar de la Renta floral-print dress for Joe Biden's 2020 victory speech. However, there was one instance where her go-to aesthetic failed her: the floral dress she donned for her and the former president's appearance on "Dick Clark's New Year's Rockin' Eve with Ryan Seacrest" on the last night of 2023. Jill clearly wanted to go for something festive for the holidays but ended up straying into tacky territory in a gaudy black dress designed with a sheer neckline and sleeves and covered with colorful jeweled flowers, as seen in the video shared by the program on Facebook.

Considering Jill had worn an elegant blue dress and a chic black frock with silver detailing during her previous appearances on the show, the bejeweled outfit was far too much in comparison. Dr. Biden's New Year's Eve dress was met with mockery on X (formerly Twitter), particularly from Trump supporters, with one claiming that it "looks like Christmas gift wrap" and another describing it as "a holiday Fruitcake dress," according to Newsweek. A third X user had harsh words for Jill's overall style, commenting: "She is just a trainwreck when it comes to fashion." Ouch.

It's unclear if Jill picked the outfit herself, but during this time, she was already working with her unofficial stylist and fashion adviser Bailey Moon, so the blame may not solely lie on the first lady.

During her final year as first lady, Dr. Jill Biden stepped up her fashion game and gave us slay after slay. She kicked off 2024 on a great note when she was seen exiting Air Force One wearing a hot pink maxi dress and Barbie-pink blazer in early February. A few months later, she stunned in a velvet, navy blue Schiaparelli gown during a state dinner in Paris hosted by French President Emmanuel Macron and first lady Brigitte Macron in honor of the Bidens. However, she broke her win streak with a questionable outfit choice in March 2024. For her appearance at the 2024 Human Rights Campaign dinner in Los Angeles, Biden wore a long-sleeve bodysuit embroidered with multi-color sequins all over, paired with black pants and a wide black belt. While there was nothing wrong with the pants and belt, the problem was her top, which, in certain angles, looked like it was covered with small holes and could trigger someone with a severe case of trypophobia.

Biden likely picked the ensemble with the help of fashion adviser Bailey Moon. The stylist told Vogue in January 2025 that when choosing the first lady's look for a specific event, they keep in mind that all the details in an outfit "are part of the conclusion people make of an event or an appearance." It's unclear what message they were sending with the rather bizarre top, but Biden's outfit appeared to be part of her commitment to promote American fashion labels and designers. The bodysuit and pants were the work of Sergio Hudson, an American fashion designer who also dressed Michelle Obama. While discussing Biden's fashion philosophy as first lady, Moon explained: "It was important to underscore her appreciation for and the value of American craft."