First Lady Fashion Fails We'll Never Forget

While first ladies often have a busy schedule revolving around hosting, volunteering, advocating for various causes, and traveling, they also often have to face public scrutiny. After all, the position comes with endless cameras, public appearances, and practically no privacy. With that, what they wear is often dissected and judged, even though they undeniably have access to stylists and a glam team who can help them look their best. "There is no one goal or message that FLOTUS is trying to achieve through her dress," historian and author Einav Rabinovitch-Fox told the BBC in 2025. "Each first lady is different, and her use of clothing is different." However, every now and then, they also experience a memorable fashion faux pas, which brings us to today's topic: first lady fashion mistakes.

Now, some of the ladies simply wore the wrong look to the wrong occasion, while others tried to send a message that didn't land, and others picked clothes that didn't suit them. From Melania Trump to Michelle Obama, none of the recent first ladies have been totally immune to fashion mistakes, but at the end of the day, they hopefully learned from it. The only exception is Hillary Clinton, whose love for dramatic ruffles has remained strong. Frankly, there's also plenty of power in rocking something you love, no matter what anybody else says. 

During Joe Biden's campaign, Dr. Jill Biden decided to send a message with her dress. The first lady showed up to a Raleigh, North Carolina, post-debate campaign in June 2024 in a dress that had the word "vote" written all over it. While we love the fact that she wanted to encourage people to vote, from a fashion standpoint, this dress was a pretty horrendous choice. The piece is by "Project Runway" winner, designer Christian Siriano, and while he usually stands behind avant-garde and fashion-forward pieces, Jill Biden's dress isn't a great example of his work.

So, let's break down all the things that make this look like a fashion faux pas. First of all, the print is tacky; writing "vote" all over the fabric isn't the chicest way to urge people to act on their constitutional right. Instead of writing it all over the dress, a bag or scarf with the same message would have not only sufficed but also resulted in a better fashion moment. A version of the dress is for sale on Christian Siriano's website for around $4,200, and for that price, we'd expect an exquisite fashion moment, not a basic midi dress.

We all know that President Donald Trump is a major fan of baseball hats, but we rarely see his wife Melania Trump rocking them. So when she does, all eyes are undoubtedly on the design she chooses. In August 2017, the first lady was photographed returning to the White House while wearing a hat that had "FLOTUS" written on it.

Now, considering that Melania is one of the more fashionable first ladies, a fashion mistake like this one is kind of out of character. After all, we all know who she is, so there's absolutely no need for a hat like that. On the other hand, Melania Trump is known for bold looks that feel completely out of place, and as her husband is big on hats, perhaps he gifted her this one. If that's the case, she was just showcasing his present. The rest of her outfit is simple and chic, and had her hat been a classic black one, this would have been a great look!

In April 2009, Michelle Obama and her husband President Barack Obama attended a royal meeting at Buckingham Palace in London, England. For the occasion, Michelle wore a dress that looked like a simple midi skirt and a white top, and she paired it with an unbuttoned black cardigan. Unfortunately, Michelle Obama's untraditional outfit while meeting Queen Elizabeth will always haunt her. 

As soon as photos from the meeting were made public, the first lady was heavily criticized for her look. The outfit itself wasn't awful, but it certainly wasn't appropriate for the occasion. Meeting Elizabeth II, then a monarch, was a big deal, no matter who you were, and a more formal outfit was expected of the first lady. And while we'll never know how Queen Elizabeth felt about the fashion moment, there's no doubt that Michelle learned from it, as she hasn't repeated her mistake.

Over the years, it became clear that Melania Trump's bold, wide-brimmed hats would always steal the spotlight. And while the accessory is a look the first lady pulls off with ease, sometimes she seems to wear them to hide her face from the public. Of course, being in the spotlight can be overwhelming, but there are certain occasions when one expects to see the face of the first lady — her husband's inauguration being one. 

On January 20, 2025, Melania showed up to Donald Trump's inauguration ceremony for his second term in a sophisticated coat by Adam Lippes. "The tradition of the presidential inauguration embodies the beauty of American democracy and today we had the honor to dress our first lady, Mrs. Melania Trump," the designer revealed (via VOA). "Mrs. Trump's outfit was created by some of America's finest craftsmen, and I take great pride in showing such work to the world." Melania paired the outfit with a hat by designer Eric Javits, and while the entire look wasn't bad, the first lady's face was pretty much hidden from cameras the entire time. "My art background gave me an edge in bringing harmony and balance to the face by creating hat shapes that would flatter and enhance every kind of face," the designer shared (via Wavy). "In this specific case that was not difficult to do, in that Mrs. Trump is blessed with great bone structure, beauty and a wonderful sense of style." Yes, wide-brims are Melania's thing, but Inauguration Day should have been an exception — and she would have looked great without her hat or with one that had a slightly smaller brim.

In the 2000s, Melania Trump rocked plenty of dramatic looks that all had one thing in common: ruffles. But as the first lady, her fashion became a lot tamer. While the Slovenian-born former model still loves fashion, sometimes we can't help but wonder what draws her to certain statement pieces. A great example is the red-bow dress she wore on July 4, 2018.

We get it — she wanted to make sure she wore red, white, and blue, but there are chicer ways to pull it off. Melania wore a Ralph Lauren shirt dress that retailed for $2,790, and she paired it with a red-bow belt that was way too big, especially considering that belts over dresses had been out of style for years at that point. Perhaps a more delicate, thin belt and a red purse would have elevated this look; instead, it earned a spot on our list.

Thanks to her past, Melania's fashion choices often come under scrutiny. "Melania is not known as a great speaker, which made her fashion choices even more important, because many times, that was her form of speech," Einav Rabinovitch-Fox explained to the BBC, adding that "as a former model, she is of course not a stranger to fashion, and she knows very well how to use clothes." This, of course, makes Melania's fashion mistakes even more unexpected. 

While statement belts have been trending again in 2024, the truth is that the way they were worn in the late 2000s has stayed in the past. A great example of peak statement-belt fashion of the late aughts is Michelle Obama's October 2009 look. The first lady wore a thick bedazzled black belt right under her bust, which sat over both her blouse and unbuttoned cardigan.

While "belts over dresses" is a trend that can be executed stylishly, "belts over cardigans" is a look that will always feel awkward. Had the first lady worn a dress instead of the blouse and the belt under her cardigan, this look could have passed for cute. But like this, it undeniably deserves a spot among the other first lady fashion crimes. Luckily, the FLOTUS has come a long way in her fashion journey, and today, we love how Michelle Obama shows off her killer legs. 

Speaking to Oprah Daily in 2025, Michelle revealed that she quickly realized fashion played a major role in the messages she wanted to send as first lady. "As women, our looks are always going to get dissected under a microscope. I made it a point to stay out of that conversation while we were in the White House because I wanted people to focus more on what I was saying than what I was wearing," she explained. "But the truth is, how we choose to show up really does matter. We do ourselves no favors if we try to act otherwise. Style is a language of its own — a way to instantly send a message about who you are, what you care about, and what you believe."

It's not too common to see first ladies at the Met Gala, so when one does attend, all eyes are on her. Over the years, Melania Trump gave us plenty of Met Gala looks, making her the most associated FLOTUS with the prestigious fashion event. Hillary Clinton also attended the Met Gala, but her choice of attire in 2001 isn't remembered for how fashionable it was.

That year, the theme of the evening was "Jacqueline Kennedy: The White House Years," and while this should have been an easy task for a first lady, Hillary didn't really show off her fashion talent. The former United States Secretary of State showed up on the red carpet in a shiny cheetah-print gown and a bronze shawl that matched the underskirt peeking at the bottom. The entire look was too shiny and bold, not reflecting Jacqueline Kennedy's sophistication at all. Speaking to the BBC, Einav Rabinovitch-Fox revealed that Hillary "had a conflicted relationship with fashion as a first lady, and only began to understand its role and importance when she became a political actor in her own right."

Melania Trump is no stranger to controversial fashion moments, and in June 2018, she seemingly used her jacket to send a message to the public. Melania was photographed entering a vehicle after leaving a detention centre where children were held after they had been taken away from their parents. The separation of children from migrant families caused a public upheaval, and Melania was visiting the location to see the conditions in which the children were kept.

However, the back of her jacket had "I really don't care, do u?" printed on it, which led many to believe that this was her stance on the entire situation. Melania's communication chief stated that it was "just a jacket," but it's difficult to believe that nobody thought about the message on its back (via BBC). However, later on, Melania revealed to ABC News that the jacket was actually intended as a message, just not for the children. "It's obvious I didn't wear the jacket for the children, I wore the jacket to go on the plane and off the plane," the first lady shared. "It was for the people and for the left-wing media who are criticising me. I want to show them I don't care. You could criticise whatever you want to say. But it will not stop me to do what I feel is right." Regardless of why she wore the jacket, it ended up becoming an insensitive way of using fashion to express herself — and as the first lady, Melania should have known better.

While Hillary Clinton's style tends to be simple and classic today, back in the early aughts, the first lady was all about statement pieces. And one look she simply couldn't get enough of was ruffles. In particular, the politician was fond of pirate shirts, which had dramatic ruffles around the collar and sleeves.

In 2001, she attended the VH1/Vogue Fashion Awards in a simple black pantsuit with a white pirate shirt underneath. Now, while pirate shirts can be fashionable and fun, this first lady simply doesn't have a great record when it comes to pulling them off. For the awards show, she clearly wanted to add a more casual element to her look, but instead of being cool, she ended up looking like she was wearing a costume. Unfortunately, this wasn't the last time Hillary opted to go for a ruffled look.

In 2003, Hillary Clinton attended an AmfAR Benefit which was honoring Richard Gere, Lorne Michaels, and Anna Wintour. For the occasion, the first lady decided to go with a '90s-looking blue-velvet gown. In theory, this should have been a look that aged well, but in reality, Hillary's love for ruffles ruined it. Similar to her VH1/Vogue Fashion Awards outfit, the gown had ruffles around its collar and sleeves.

This time, however, the ruffles were in a different material and a slightly more vibrant shade of blue, making them stand out even more. Considering the velvet fabric of the gown, this piece simply had too much going on, and Hillary ended up looking like she borrowed the dress from one of the "Hocus Pocus" Sanderson sisters. However, as Hillary has been known as someone who prefers pantsuits over dresses, it is nice to see that every now and then, she opts to switch it up. In fact, in 2007, designer Donatella Versace suggested that the politician should have more fun with her look. "I can understand (trousers) are comfortable, but she's a woman, and she is allowed to show that," she said to the German newspaper Die Zeit (via Reuters). "She should treat femininity as an opportunity and not try to emulate masculinity in politics."

Michelle Obama received quite a bit of backlash in April 2009 when she showed up to volunteer at the Capitol Area Food Bank for Feeding America in a pair of sneakers that were rather expensive. While the first lady wore a casual white top, an unbuttoned cardigan, and gray skinny pants, it was her shoes that quickly became the topic of conversation. Michelle wore a pair of Lanvin sneakers that retailed for $540 at the time.

"She used them to walk the dog," Maggie Rodriguez, the co-anchor of "Early Show," commented at the time, per CBS. "I think she's worn them — she says she wakes up at 5:00 in the morning to walk her dog. And her response to all this was, 'they're just shoes,' but they're expensive shoes," she added. So while this outfit isn't necessarily bad, it's still a fashion fail as her footwear choice made the fashion moment completely tone-deaf. In particular, her choice of sneakers came as a surprise as Michelle was known to be a first lady who wore affordable looks. "Coming to the White House in the midst of an economic crisis, Obama became known to present an accessible image, wearing off-the-rack popular brands like Target and J Crew, while supporting young American designers, who often saw a boost to their business after Obama wore their design," Einav Rabinovitch-Fox told BBC.

Now, if you weren't some more White House fashion, be sure to also check out the 12 first lady looks that sparked fashion moments!