The Most Controversial Outfits Ever Worn By First Ladies

There are few people more visible in American politics than the first lady of the United States (FLOTUS) and even fewer who are seen as style icons in their own right simply for being in their particular position. Dolley Madison perhaps set the trend for fashionable first ladies, while Jackie Kennedy's impact on style during her time in the White House is still analyzed today. Even if it shouldn't be the case, the first lady is often viewed as an extension of her husband, the U.S. president, and as such, any woman married to a serving president is required to maintain a certain sense of style and fashion. Whether she wants to deal with it or not, FLOTUS has to look good. Simply being presentable is never enough.

Each FLOTUS is different, and the styles of these women have been received differently by the American public, resulting in some truly controversial outfits throughout American history. Many first ladies over the years have been the subject of endless conversations for their fashion sense, including the classic styles of Kennedy, the uber-glam of Melania Trump, the style evolution of Michelle Obama, or the steadfast loyalty to the pantsuit that Hillary Clinton managed to maintain. One thing they all have in common is the scrutiny some of their sartorial choices faced. From Obama's sleeveless dress to Trump's careless jacket pick, these are the most controversial fashion statements from several first ladies. 

Current First Lady Melania Trump lives an incredibly lavish life — which why it was a bit of a shock when she chose to wear a $39 Zara jacket on her way to visit the Upbring New Hope Children's Shelter in McAllen, Texas, in June 2018. Trump's spokeswoman said that the jacket's text wasn't a message despite the "I really don't care. Do u?" text, but in an interview with ABC News in October 2018, Trump herself said it was indeed "for the left-wing media who are criticizing me."

During her time as FLOTUS, Michelle Obama had scandals she just couldn't escape. Obama made a gaffe when she attended an event at the Capital Area Food Bank in Washington, D.C., in May 2009, wearing a pair of $540 Lanvin sneakers. Her casual display of wealth didn't sit well with some, including CBS News' "Early Show" co-anchor Maggie Rodriguez, who said: "She used them to walk the dog. .... her response to all this was, 'They're just shoes,' but they're expensive shoes."

There are many tragic details about Jackie Kennedy's life, and if there's one outfit that is associated with Jackie, it's the double-breasted pink wool suit she wore the day that her husband, President John F. Kennedy, was assassinated. The pink suit became controversial after Kennedy herself refused to change out of it. According to People, historian Steve Gillon said: "She went out in her blood-stained suit and stood next to Lyndon Johnson," even though another outfit had been prepared for her.

For Melania Trump, every event is one where you need to make a splash — which is exactly what she did when she arrived at the 2017 G7 summit in Italy wearing a $51,000 Dolce & Gabbana coat. Trump's decision to wear it at the event wasn't particularly well received, and D&G attempted to sell $245 #BoycotttDolceandGabbana T-shirts in response to the criticism. Of course, they were already dealing with having been called out for agreeing to dress Trump in the first place, according to Teen Vogue.

Hillary Clinton has been through a stunning transformation over the years, and she's been a trailblazer for much of her life — which includes her personal style. Known (and memed) for her love of pantsuits, Clinton was the first FLOTUS to wear one instead of a dress for her official White House portrait, which was unveiled in 2004. According to her 2017 memoir "What Happened" (via CNN), Clinton "thought it would be good to do what male politicians do and wear more or less the same thing every day."

Humanitarian and activist Rosalynn Carter served in the first lady role from 1977 to 1981 during the presidency of her husband, Jimmy Carter, and she made something of a major style gaffe when she wore a blue and gold chiffon dress to her husband's 1977 inauguration ball. Rosalynn was criticized at the time for having already worn the piece to her husband's inauguration ball as Georgia Governor in 1971. The trend at the time — and since — is for a first lady to wear something both new and custom-made for her.

Nancy Reagan was known for her classic, cinematic style. A former MGM contract actress, Reagan ensured every one of her fashion choices was picked to be as photogenic and telegenic as possible. At her height of 5-foot-4 and size 2 frame, every outfit was designed to show off her figure as much as possible. Cue her hand-beaded gown, with its one-shouldered design and simple silhouette, for the 1981 inaugural ball. While beautiful and classic in color, Reagan caused a stir amongst the press because of the dress's extravagance. 

Sometimes, an outfit is controversial not because of what it looks like, but because of its circumstances. Betty Ford experienced this when she was overtaken by whimsy while saying goodbye to White House staff in 1977, deciding to do something she'd always wanted to do — dance on the Cabinet Room table. Shoeless in a pair of casual slacks, Ford took center stage on the oval mahogany conference piece. Per the Smithsonian magazine, White House photographer David Hume Kennerly said: "Very few women have had a seat at that table ... she was tap-dancing in the middle of this male bastion."

Jackie Kennedy made several trends and designers popular thanks to her iconic style. Once, a simple picture of Jackie and her husband, John F. Kennedy, on vacation in Massachusetts caused quite a stir, simply because of her decision to wear pink pants. Her husband was then only a presidential nominee, but Jackie's sartorial choices were already becoming quite the subject of conversation. At the time, the New York Times published a piece referencing the "shocking" pant color, suggesting that something as small as the bright hue could result in a "vast political consequence."

On her first solo trip abroad as FLOTUS, it's no surprise that Melania Trump would treat the occasion as another chance to play dress-up. On the final day of her trip, during a visit to a national park, Trump chose to wear a colonial-era white pith helmet along with her white shirt, khaki trousers, and boots. The issue was that pith helmets were typically worn by colonial powers across Africa, Asia, and the Middle East, and became a symbol of oppression, according to The Guardian, which didn't go down well.

First Lady Laura Bush made the cardinal sin of wearing the same thing as another woman in 2006 when she and her husband, then-President George W. Bush, attended that year's Kennedy Center Honors event. Dressed in a stunning red-patterned Oscar de la Renta gown, Bush was horrified to realize that not only she, but three other women had also been enamored with the same outfit. Luckily, Bush had another outfit to change into, but not before the two-piece red number was captured for the Christmas card photo, according to Glamour.

All the way back in 1992, presidential hopeful Bill Clinton and wife Hillary Rodham Clinton were touring across the country, and decided to play a round of mini gold at a stop in Illinois. Former lawyer Clinton marked the occasion wearing a blue-and-white, long, striped sundress. Many years later, Clinton told Us Weekly (via Times of India) that she "would never forget that day" and is physically repulsed thinking about her dress choice — proving that sometimes only the wearer has to hate the outfit for it to cause a reaction.

Dolley Madison is known as having been friendly, warm, and quite the experienced hostess, both before and during her husband's time as the U.S. president in the early 1800s. Having been raised as a Quaker, Madison was used to modest clothing in dull colors. But when she left the faith, she took the opportunity to embrace the fashion of the times — which included showy, low-cut dresses. Apparently, this created quite an impression and created a shock for her fellow Quakers.

One would think that a vacation is exactly the time when you don't need a strict dress codes, but apparently if you're the FLOTUS, there's absolutely no such thing. Even while taking a break from her duties, such as her passion for improving children's health, all eyes were on Michelle Obama as she stepped off Air Force One wearing a pair of gray shorts. Speaking about it in an interview on "106 & Park" (via Today), Obama said that the shorts "created a huge stink," but she stood by her decision to wear them.

Some outfits are bizarre, and some are poorly conceived — which is what Melania Trump discovered when visiting Texas in the aftermath of Hurricane Harvey. Trump wore a black cap emblazoned with "FLOTUS," in case anybody needed a reminder. In solidarity, the president wore a large "USA" cap, even though hats are the one thing Donald Trump is supposed to never wear. Many were left flabbergasted, including British journalist Krishnan Guru-Murthy, who tweeted: "Melania Trump is now thoughtfully wearing a hat saying FLOTUS so we know who she is."

Wearing all black is a classic look and also one that's easy to put together when you're away from your usual wardrobe. So Hillary Clinton doesn't exactly seem to have committed some kind of cardinal sin when she chose to wear three all-black outfits during a two-day trip to Japan in April 1996. According to The Washington Post, however, Clinton "baffled the Japanese" with her successive days of black ensembles, with some questioning why she was dressed as if preparing for a funeral.

As the wife of the 16th U.S. president, Mary Todd Lincoln tended to favor big ball gowns that sat off the shoulders and had long trains for her signature look. But according to Time Magazine, each of these ensembles cost up to $2,000 — equivalent to nearly $80,000 today. Her husband's advice was that she show "a little less tail and a little more neck", but this kind of opulence wasn't received well by many at that time due to the Civil War taking place.

Melania Trump has shown off her most boring outfits, but one occasion might have been the right time to tone things down. At the United Nations in 2017 to make a speech about bullying and child poverty, Trump wore a pink dress from Spanish fashion house Delpozo worth almost $3,000. Her outfit very much didn't fit the theme, and the decision to show off her wealth while stating "no child should ever feel hungry, stalked, frightened, terrorized, bullied, isolated or afraid" was met with ridicule online — one X user compared her to Violet Beauregarde. 

The official White House portrait is a big deal, and many first ladies have set tongues wagging for their choices. For Michelle Obama, her official portrait was met with criticism for being "too informal and out of season," according to ABC News. Obama was known at the time for favoring sleeveless outfits, so some were even surprised that her black dress in the portrait sparked such arguments of controversy — but it does seem to be just the endless curse of the FLOTUS that the outfit is always a news story.

Edith Roosevelt, wife of President Theodore Roosevelt, didn't much care for being the center of attention and preferred to stay as frugal as possible — which meant getting thrifty as much as she could. According to the Reading Eagle, the first lady reused outfits on multiple occasions and described them differently to the press each time to make it seem like she had a larger wardrobe than she did — this only added to criticism that she was too private and almost royal for a first lady. Edith would also frequently recycle material from her old wardrobe to create new clothes.

Over the years, Donald Trump has uttered some of the cringiest comments about women in his orbit, with one of the most famous being his grabbing women "by the p***y" comment. It's unfortunate that not long after these comments were unearthed, Melania Trump chose to attend one of the 2016 Presidential Debates in one of Gucci's classic styles, known as the "p***y-bow blouse." Whether ironic or unfortunate, the blouse caused some commotion, according to The Hollywood Reporter, even if Melania hadn't intended to call attention to the scandal.

Frances Cleveland, wife of 22nd and 24th U.S. President Grover Cleveland, faced ire from some tough opponents in her day. What is considered appropriate dress for women has changed so much over the years that her particular scandal probably wouldn't cause any kind of ruckus now. But in the late 1800s, she faced criticism from the Women's Christian Temperance Union for her love of outfits that showed off her shoulders, according to Business Insider. The union even petitioned for her to stop wearing them altogether, but the first lady refused.

It's a classic image of Hillary Clinton; she's sat talking to other students at Wellesley College, every bit the educated hipster in her white button-down shirt, big glasses, intensely-striped pants, and sandals. No doubt it was a good look at the time, but when discussing her worst looks with US Weekly (via the New York Times) in 2008, Clinton didn't remember them favorably. However, in her own words, "it's not my fault, it was the 60s", proving that trends don't always age well.

It's not the first time Michelle Obama has been criticized for being too casual — as we noted, her lack of sleeves caused a stir. But during a visit in 2009 to the United Kingdom to meet Queen Elizabeth II, Obama stood with her husband and the late Queen for pictures wearing a black skirt/white top/black cardigan combo, resulting in her outfit being directly compared with Queen Elizabeth II's colorful get-up. Obama's outfit was criticized for lacking luster, with Vanity Fair describing it at the time as, "Placid for the palace with perhaps a dash of state funeral?"