The Most Scandalous First Lady Outfits Ever Worn

From the criticism surrounding Melania Trump making a fashion faux pas at Jimmy Carter's funeral to Michelle Obama's extremely expensive outfits, we can see that it's not easy for a first lady to avoid scandal.

"For a lot of Americans, the first lady represents the administration," Valerie Steele, chief curator and director of the Museum at the Fashion Institute of Technology, told Women's Wear Daily, "so she should represent that administration and more generally represent the United States in the world. We expect her to live up to that. That's her job in a sense." This job, it seems, involves fashion. While their looks are also often praised, first ladies in the Land of Liberty can't shake the scrutiny that comes their, and their stylists', way when they step out in public.

From Jacqueline Kennedy's controversial colorful trousers in the 1960s to Frances Cleveland shocking the nation in the 1880s with by showing some skin, these are some of the most scandalous first lady fashion moments in history. 

One of America's most glamorous first ladies was Jacqueline Kennedy Onassis, the wife of slain president John F. Kennedy. A big part of this former first lady's legacy is the mark she left on fashion history, but perhaps one of the untold truth of Jackie O is that not all of her outfits were slam dunks. 

While modern audiences may view these peony pink hip huggers that Jackie wore on the campaign trail in 1960 as a super chic take on color blocking, contemporary audiences weren't so convinced. At the time, a correspondent for The New York Times, Martha Weinman, wrote about the first lady's fashion choice, dubbing Kennedy's bold color combos "something of possibly vast political consequence." She theorized that the then-presidential nominee could be in danger of losing his bid for the White House if public opinion were to turn sour on his wife's sugary sweet fashion choices. Her article essentially questions if we can take colorful women seriously.

Despite the apparently shocking outfit, she sailed right on into 1600 Pennsylvania Avenue with her suitcases full of bright hues, including the famous pink pillbox hat that would go on to become a symbol of the Swinging Sixties in America.

Red is not only the signature color of the Republican Party, but it also was the go-to hue for First Lady Nancy Reagan. The wife of President Ronald Reagan donned shades of burgundy, cherry, and carmine so often that her name eventually became synonymous with bright red Republican fashion. However, despite Mrs. Reagan's clear love for clothing, her passion didn't shield her from a sartorial scandal or two. 

Throughout her husband's two terms in office, Reagan found herself embroiled in battles with the media after she was caught borrowing clothes from luxurious fashion brands and refusing to either report it or return the item. The most surprising of Reagan's fashion faux pas, though, occurred when the queen of the conservative party wore a sparkling, one-shouldered gown to the 1981 inauguration ball following her husband's swearing-in ceremony.

Though the gown fit the dress code of the event and designed by the expert hands of Greek designer James Galanos, the amount of skin that was on display was shocking for a first lady whose name was synonymous with old-fashioned family values. In 2017, The Washington Post looked back on Reagan's fashion, concurring that this slinky white number was, in fact, "surprisingly bare for a first lady." Despite the scandalous cut of the gown, one cannot deny that Nancy's adventurous approach to dressing left a mark on first lady fashion.

Before Hillary Clinton entered the White House, first lady official portraits were a parade of petticoats, corsets, and taffeta gowns. However, the wife of then-President Bill Clinton changed the game when she dressed in a striking all black pantsuit for her official White House portrait in 2004. Clinton was so committed to the game that she even wore a pantsuit at the unveiling ceremony, except this time it was in a baby blue hue. 

Despite the expert cut of her suits, it was considered pretty scandalous for a first lady to, quite literally, wear the pants. The divide between career-women like Hillary and women who chose to be homemakers was once so wide that the first lady was forced to apologize to homemakers on the campaign trail. During her husband's first presidential campaign in 1992, Clinton told a reporter, "I suppose I could have stayed home and baked cookies and had teas, but what I decided to do was to fulfill my profession." This, paired with her more masculine style of dress, incensed many American homemakers. 

Today, Clinton's love of a good colorful pair of trousers and matching suit jacket is not so scandalous. And it's so beloved by many Democratic hopefuls that they donned their very own bright and bold pantsuits to the polls in 2016. After casting their vote for the fashion-forward nominee, many netizens posted a pantsuit selfie alongside the hashtag #PantsuitNation.

While some first ladies have signature colors and others have favorite designers, Michelle Obama was known for her extensive sneaker collection. Often, this comfy alternative to kitten heels and pumps contributed to her approachable vibe, allowing the first lady to seem like a fellow suburban mom taking a stroll around the block rather than one of the most powerful women in the nation. 

However, this folksy styling technique backfired during a public engagement in 2009. While standing atop a stage at a D.C. food bank alongside then-Second Lady Jill Biden to discuss the issues facing impoverished Americans, reporters took notice of Obama's slate gray and shiny-tipped sneakers. While the first lady's footwear matched her capris and her laidback, argyle cardigan, something about those metallic kicks just seemed a bit too posh. 

Scandal ensued when the world learned the shoes came from the luxury brand Lanvin and bore a shocking price tag of $540. In another context, this might not have been a faux pas. Perhaps if Obama wore them on a school run with her two daughters or to a casual event with other dignitaries, no one would've batted an eye. However, the irony of the first lady donning such luxurious footwear while speaking at a food bank caused many Americans to roll their eyes. When confronted about the scandal, Obama's team curtly replied, "They're shoes" (via ABC7).

The Trumps are no strangers to first couple fashion mishaps. However, no joint faux pas has incited as much ire as this incident from first lady Melania Trump. On her way to board a flight in August 2017, the first lady was photographed wearing an olive green army jacket, aviator sunglasses, and sky-high heels.

So what's all the fuss about? The ensemble might sound on par with Melania's style, but it is the tragic context that makes this such a sour sartorial choice. When the first lady was photographed wearing these impressive toe-pinchers, she and President Trump were en route to visit Hurricane Harvey victims in Texas. 

Labeled "one of the largest disasters America has ever faced" by Governor George Abbott, Hurricane Harvey took the lives of at least 89 people, with thousands more having lost their homes. For a woman who is meant to represent the heartbeat of the nation, you would be right in expecting her to wear an ensemble that communicated a bit more humility and approachability in this instance. Instead, the first lady opted for pumps better suited for the Met Gala. Following the incident, Vanity Fair published a scolding article with a headline that reads, in part, "Who Wears Stilettos to a Hurricane?" Citizens were also unimpressed, with one commenter, Todd Stashwick, writing on X, formerly Twitter, "Nothing says I'm in touch with the people like [this]" (via AOL).

It was the graphic jacket heard 'round the world — Melania Trump's militaresque green accessory that posed the question, "I REALLY DON'T CARE DO U?" on the back in a white graffiti-style font. As the first lady climbed into a black SUV after touching down in McAllen, Texas, the paparazzi snapped away at her back, and scandal ensued. 

As Melania was in Texas with the sole purpose of visiting the New Hope Children's Shelter, located on the Mexican-American border, many angry internet users and political pundits alike claimed that the first lady's graphic coat was an indirect response to the plight of these migrant children. Somber and respectful would have been the right tone to strike for this occasion, but instead, the first lady chose a crude and mocking article of clothing that was entirely too insensitive for the occasion. 

Melania tried her best to go on the defensive, claiming that her jacket was in no way related to current politics, but the damage had already been done. The first lady later claimed that the message on her jacket was for "the people and for the left-wing media who are criticising me" (via BBC). She added, "I want to show them I don't care." Regardless of the intended target, Melania's message was heard loud and clear. 

Not all scandalous fashion moments are the results of faux pas or wardrobe malfunctions. No, many women who once found themselves in the middle of a sartorial storm would now be applauded for their bravery in breaking societal norms. Take former First Lady Betty Ford for example. Standing by her husband President Gerald Ford's side in the 1970s, Ford was in the White House on the very cusp of a feminist revolution. 

And while Mrs. Ford was never spotted at any bra-burning protests, her feminist politics were on display in other ways. At a time when respectable women were expected to cover up and wear demure knee-length (if not longer!) dresses, Ford broke the mold by wearing trousers and pantsuits. However, she wore them in private. One image of the former first lady wearing pants does exist, though, and at the time, its contents were scandalous. 

Snapped by photographer David Hume Kennerly on January 19, 1977 — as the Fords were busy moving out and making way for the new incoming president — the image shows Mrs. Ford standing atop a long wooden table in the Cabinet Room, striking a playful pose. In old age, the former first lady recalled, "I walked over to the West Wing to say goodbye to members of the staff who had served President Ford so well. ... I passed by the empty Cabinet Room and thought, 'You know, I've always wanted to dance on the Cabinet Room table.'

Long before there was Melania Trump's controversial glamor or Barbara Bush's frumpy first lady aesthetic, there was the scandalous Frances Cleveland. Believe it or not, even when the American public had no access to candid paparazzi pics, Mrs. Cleveland still managed to invoke ire with her fashion choices.  

The first lady was only 21 when she married the 49-year-old President Grover Cleveland in what is still, in 2025, the only presidential wedding to take place on the actual ground of the White House. The new Mrs. Cleveland's young age was already scandal bait for the press, but it was when the new first lady began to dress exactly like the 21-year-old she was that the more conservative parts of America were sent into outrage overdrive. 

Always on the cutting edge of women's fashion of the day, Cleveland was known for wearing gowns that showed off her bare shoulders, the tops of her arms, and a whole lot of bare neck. And while this might not be a headline-making way of dressing in the modern day, in the 1880s, this was still considered risqué. Women, especially women in politics, were expected to cover up. The Women's Christian Temperance Union said as much when they drafted a petition imploring the first lady to cease wearing such sexy and sinful frocks. Ever the rebel, Cleveland ignored the petition and continued to dress how she pleased.  

Nairobi, Kenya, was the site of one of first lady Melania Trump's worst fashion blunders of all time. In 2018, social media flamed the Slovenian-born public figure when she was spotted on a safari with Kenyan officials wearing a particularly old-fashioned get-up. Her white button-down shirt and khaki riding pants were a little over-the-top, but it was Trump's white pith helmed that particularly incensed the internet.

Worn by military officers and colonial explorers throughout the 1800s, this style of hat is an undeniable representation of a period in African history that was defined by racist, oppressive violence. The pith helmet was believed to have the power to protect fair-skinned Europeans from what was termed "tropical solar radiation."

In response to Melania's choice of headwear, one netizen tweeted, "How 'imperialist colonial oppressor' can you get?!" while another wrote, "That pith helmet you have carried was used by colonialists during the dark days. Doesn't sit well with us Africans." As another Twitter user's post illustrates, Trump's decision to wear a pith helmet in Nairobi was deemed by the world as "more than a silly sartorial choice," but as "a reflection of her outdated understanding of Africa." Whether intentional or not, this was not a good look for a first lady whose tour of the African nations of Ghana, Malawi, Kenya, and Egypt was meant to promote child welfare, education, and wildlife conservation, not stir up controversy.

Barbara And George H. W. Bush's epic love story is one for the ages. The 16-year-old Barbara was wearing a jolly green gown when she met the 17-year-old future president at a Christmas dance. Decades later, the two would be photographed dancing together once more, but this time on a much bigger stage. That's right, we're talking about the inauguration ball in 1989. 

Although Barbara, who had just become the nation's first lady, looked beautiful in her midnight blue gown made of velvet and satin, her fashion choice caused some eyebrows to rise. The long-sleeve dress was designed by Arnold Scassi, who famously described his client as "the most glamorous grandmother in the United States." 

However, glamorous though she may have been that night, tabloids the next morning were shocked to learn that the Republican party's crowning queen had celebrated by wearing the colors of their rival political party. While the Democrats have long been associated with blue, it's red that is the calling card of the Republicans. That wasn't all Barbara caught flack for. At the dawn of her husband's presidency, her dresses were deemed "dreadful" (via Los Angeles Times). Bush herself was called "grandmotherly looking." Despite party politics and the fashion snoots, Barbara danced the inaugural night away, clad in sapphire and smiles.

While this former first lady is well known for her intellect and skills at public speaking, Michelle Obama's arms once had fame all their own. While many praised the political figure for her toned physique and clear upper-body strength, others took Michelle's biceps quite personally and found her penchant for wearing sleeveless gowns offensive. 

The outrage reached a fever pitch when the then-first lady wore a sleeveless a-line dress in her first official White House portrait in 2009. One naysayer was Andy Card, the chief of staff to former Commander in Chief George W. Bush. The White House insider responded to the portrait by saying, "There should be a dress code of respect" (via The Guardian).

Despite the public outcry, Michelle simply shrugged off the scandal. In her 2018 memoir "Becoming," Obama wrote, "I wore a sleeveless aubergine dress to Barack's address to the joint session of Congress and a sleeveless black sheath dress for my official White House photo, and suddenly my arms were making headlines" (via Elle). Change up her dress code? Not a chance. Obama simply let the headlines roll.