The Worst-Dressed First Ladies In Inauguration History

We may receive a commission on purchases made from links.

Many first ladies have made impactful fashion statements over the years with daring outfits that captured attention for any number of reasons, from their daring design to their out-and-out messaging ("I Really Don't Care, Do U?", anyone?). The job requires careful attention to their appearance at any public event, but inauguration day is a first lady's initial chance to make a stand-out impression. Some presidential wives have made it look easy, such as Jackie Kennedy and Nancy Reagan, who both looked impeccable at their husbands' swearing-in. Nineteenth-century first ladies also had the advantage of the gorgeous styles of the time, with lacy bodices and sweeping skirts.

However, in more recent decades, we've seen almost as many misses as hits on inauguration day. Wonky color choices, poor fits, or otherwise unflattering details made the first ladies look less than their best. Here are some of the styles that get a thumbs-down from us. 

Ironically, for a woman who published a retrospective fashion memoir titled "The Look," Michelle Obama's outfits have missed the mark several times. Her selection for husband Barack Obama's first inaugural ceremony was one of them. Michelle arrived at the historical 2009 event in a wool Isabel Toledo dress-and-coat combo; the cut was splendid, but the yellow-green color wasn't a flattering look on her, and the accessories clashed awkwardly (though she does get props for wearing J.Crew gloves). Four years later, the first lady turned out for the president's second inauguration in a much smarter navy checked Thom Browne coat ensemble, set off by high boots and violet gloves.

In addition to his other accomplishments, Franklin D. Roosevelt holds the distinction of being the only president to serve four terms in office, though Donald Trump probably wishes he could do the same. His wife, first lady Eleanor Roosevelt, was no slouch herself, becoming renowned and beloved for her writings and humanitarian efforts. While she won't be remembered for her 1933 inaugural outfit — the baggy fit and droopy detail on her blouse did her no favors — the first lady herself said it best when she declared (via Biography): "No matter how plain a woman may be, if truth and loyalty are stamped upon her face, all will be attracted to her."

Hillary Clinton had two chances to wow the crowd with inaugural attire, but unfortunately, she fell short both times. When President Bill Clinton took his oath in January 1993, the former first lady of Arkansas played it safe in an unmemorable pink and gold plaid suit, with a hair-hiding blue hat as her one accessory. Kicking off her husband's second term, the future secretary of state went a little bolder with an Oscar de la Renta coat. Unfortunately, the large, formless, and monochromatic outfit seemed to swallow Clinton up, and its pastel pink coral color was a bit childlike for a woman who was trying to be taken seriously as a political figure.

In addition to the cozy coats they don for the swearing-in ceremony, first ladies commission fancy ball gowns for the parties that follow. Hillary Clinton's 1993 purple lace inaugural gown made up for her stuffy morning wear, as did Eleanor Roosevelt's silver number and Michelle Obama's one-shouldered white one. Even grandmotherly Barbara Bush looked glam in her blue Arnold Scaasi gown. Yet we can't say the same for Rosalynn Carter's choice, a chiffon dress with a full-length coat. Despite the lovely gold embroidery, the vibes of the coat were more bathrobe than ballroom. Critics found fault with it for a totally different reason: She'd already worn it when husband Jimmy Carter was governor of Georgia, and people thought the cost-conscious move was tacky.

This article wouldn't be complete without a mention of Melania Trump's appearance at her husband's second swearing-in. Polished as she was, the first lady was still one of the worst-dressed people at Donald Trump's 2025 inauguration. The dark navy shade and severe cut of her suit were a downer for such a happy occasion. And that hat! The wide-brimmed boater made the FLOTUS's expressions almost impossible to read, and led to an awkward moment when her husband tried to kiss her; netizens joked that this was the whole point of her hat. Was the somber look meant to represent Melania's feelings about being flung back into public service again? Or a prediction of her husband's plans to overhaul the country? The notoriously private first lady isn't saying.