12 Michelle Obama Looks That Completely Missed The Mark

Michelle Obama has made a stunning transformation from lawyer to first lady to style icon. During her eight-year tenure in the White House, Obama wore a glamorous array of outfits, each one seemingly more dazzling than the last. She quickly became an icon for her impeccable wardrobe, which was a reflection of her vibrant personality.

In many ways, Obama was the antithesis of her successor, Melania Trump, who remains strangely stoic and tight-lipped despite being married to the most controversial president in recent U.S. history. While Trump wore traditional designer garb during her time as first lady, Obama was always more open to experimenting with fashion and giving a platform to fledgling designers. As Jason Wu, who designed clothes for Obama multiple times, told Interview, "There's something more than just the clothes she wears that everyone relates to so much with her—people appreciate the sense of realness about her."

But Obama is proof that even the most chic style queens can have their off days. On occasion, the former first lady has sported fits that were either misplaced, ill-advised, or just plain odd. Here's a rundown of 12 Michelle Obama looks that completely missed the mark.

On election night in 2008, Michelle Obama stepped out in one of her most divisive outfits to date. She wore a black Narciso Rodriguez frock with a splattering of red that looked more foreboding than fashionable. The criss-cross design and black and red color palette appeared almost emo-adjacent (was there any self-respecting scene kid who didn't wear an edgy black and red outfit in the aughts?) and felt out of place on the momentous, history-making occasion.

The dress left fans divided, with one Barack Obama supporter lamenting to The New York Times that they voted for the Democratic nominee's policies, not his wife's dress. "I don't know what was worse, that stupid criss-cross band around the middle or that black sort of border coming up from the hem," complained another detractor. Others compared the dress to a lava lamp.

However, designer Rodriguez defended Michelle for going against the grain. "It was so controversial," he told the Huffington Post. "For me, it was so exciting to see a woman take a chance and wear something out of the ordinary ... People noticed — it was unapologetically black and red."

When her husband, Barack Obama, was inaugurated in January 2009, Michelle Obama wore an eye-catching yellow coordinate. Showcasing a tweed coat and matching dress by indie designer Isabel Toledo, the first lady evoked the chic style of Jackie Kennedy. But perhaps that was the problem: Barack's campaign was all about change, as he promised a brighter future for the American people. By wearing a retro fit, Michelle appeared to be referencing an America of yesteryear.

Moreover, her glossy white tights, the likes of which haven't been fashionable in decades, made the outfit appear even more outdated. "We have been wondering all afternoon, on whose friendly advice and when did she decide to ditch?" asked Grazia style director Paula Reed, per the BBC. Some matte hosiery would have been preferable to elevate the ensemble out of granny chic territory.

Of course, there was nothing wrong with Michelle's get-up on its own, but context is key. It would have been more apt for her to wear a trendier outfit, something that reflected the progress that her husband's campaign was espousing.

In March 2009, Michelle Obama posed for her debut official portrait as first lady. But something was amiss about her choice of attire. Obama had opted for a chic little black dress for her photoshoot, and while there was nothing inherently wrong with the outfit in and of itself, she decided to go bare-armed.

The sleeveless look was a tad too basic and informal for an official portrait, not to mention the fact that the photo-op took place in the winter. Surely the first lady was feeling more than a tad chilly in her summery number? "One reader summed it up better than most of them. She talked about how the season is winter, the occasion was business and a sleeveless dress was the wrong style at the wrong time," said the Chicago Tribune's Wendy Donahue, per ABC News.

One can't help but feel that a chic cashmere cardigan or a long-sleeved wool dress would have hit the mark for Obama's first portrait. Then again, Obama's fashion faux pas has undoubtedly become an iconic image of the uncompromising former first lady.

During Queen Elizabeth II's reign, numerous world leaders embarrassed themselves in her company. In Barack and Michelle Obama's case, it was the latter's outfit that was at the center of contention.

When meeting someone who's the epitome of aristocratic refinement, one would be expected to deck themselves out in their finest regalia. But Michelle decided to keep things super casual during her 2009 visit to Buckingham Palace. Wearing a two-tone dress under a black cardigan, she was criticized for looking too low-key in the presence of the monarch. Indeed, it did look like the sort of coordinate one might wear to Sunday brunch with pals, as opposed to being an outfit fit for (a meeting with) a queen.

The queen hardly seemed to care, however. It's been said that the Obamas were among her favorite presidential couples. In fact, when Michelle broke royal protocol by putting her arm around Elizabeth, the monarch welcomed the sweet gesture. Looking back on the incident, Michelle joked that it was her Jimmy Choo shoes, rather than her cardigan, that ruined her outfit that day, unexpectedly leading to the controversial hug. "'These shoes are unpleasant, are they not?' she said," Michelle wrote in her memoir, "Becoming." "She gestured with some frustration at her own black pumps. I confessed then to the Queen that my feet were hurting. She confessed that hers hurt, too."

During her visit to the U.K. in 2009, Michelle Obama also met with then Prime Minister Gordon Brown and his wife, Sarah Brown. Wearing a sparkly, bejeweled cardigan, mint skirt, and equally shimmery shoes, Obama looked rather out of place next to Sarah. The prime minister's wife was decidedly understated in a plain navy outfit and gray tights. One can't help but feel that the first lady should have worn this show-stopping ensemble to meet Queen Elizabeth II, and the aforementioned monochromatic coord to meet Sarah. Evidently, Obama and Sarah didn't discuss their outfits in a group chat prior to their meeting.

However, some defended the pair's mismatched ensembles. "They were never going to turn up in similar things. Their personalities are obviously so different," Vogue's Calgary Avansino told The Guardian. "But I think they both are obviously trying to send a very clear message that they can wear what the average women would wear and still look great and that they are not above it."

While in the U.K. in 2009, Michelle Obama paid a visit to the Royal Opera House, where she met with the venue's performers prior to the G-20 summit. But her outfit, which somehow managed to be at once casual and formal, appeared out of place at the historic opera house. Obama wore a fit and flare blue dress under a Junya Watanabe argyle cardigan, accompanied by a string of pearls and some matching pumps. Though it undoubtedly showcased the first lady's personality, the whole thing felt oddly preppy, almost schoolgirl-esque, as if Obama was donning a Blair Waldorf cosplay. Others compared the look unfavorably to a golfing get-up.

A visit to an opera house, particularly one as prestigious as the London venue, necessitated a more opulent ensemble. Without the addition of the cardigan, Michelle's outfit would have been on point, with the elegant dress perfect for the refined setting.

But perhaps Obama's decision to dress down was deliberate, a way of appealing to the younger generation. As communications consultant Ruth Sherman told CBS News the previous year, Obama appeared to be making a statement via casual attire. "If the Obamas are being considered the next generations of leaders, will the Obamas reflect that this generation is so much more casual? ... Are people's tongues going to be wagging or is it part of her job to appeal to that generation?" Sherman said.

Hosting then Chinese President Hu Jintao at the White House in 2011, Michelle Obama was a vision in a red gown. But upon closer inspection, Obama fell just short with this look. The point of the meeting was to bolster trade between the U.S. and China. As such, one might have expected Obama to don an American designer, or even a Chinese one such as Jason Wu, whose clothing she had previously worn. Instead, she sported a dress by British designer Alexander McQueen, a rather baffling decision given the occasion.

She was widely criticized for her stylistic choice. Notably, Oscar de la Renta argued that wearing a European brand was incongruous with the event. "My understanding," de la Renta told Women's Wear Daily, "is that the visit was to promote American-Chinese trade — American products in China and Chinese products in America. Why do you wear European clothes?" In response, Obama told "Good Morning America" (via The Week) that she was promoting policy, not fashion.

Three years later, Obama wore a de la Renta dress for the first time at a White House event. Her decision to do so was viewed as an acknowledgment of de la Renta's influential place in American fashion history, with first ladies Hillary Clinton and Laura Bush having frequently worn the designer before her.

In 2015, Barack and Michelle Obama visited Saudi Arabia following the death of Saudi King Abdullah. But the first lady seriously missed the mark with her choice of attire — or lack thereof. Michelle wore a colorful blue outfit for the occasion, but she chose not to wear a headscarf. This led to hefty criticism, with social media users accusing her of failing to show respect, particularly in light of the king's death.

At the time, it was mandatory for Saudi women to wear an abaya, a long garment that covers the majority of the body. While foreign visitors were not required to cover their hair with a scarf, some critics argued that Michelle was being disrespectful by not wearing one. "Her presence reaffirms what many women living in Saudi Arabia already knew; a Western woman can always walk around the cities of Saudi Arabia with more freedom than the locals," Hadiya Abdelrahman wrote in Quartz. Though Michelle wasn't the first foreign female guest to forgo a head scarf while meeting Saudi leaders, one could argue in favor of adhering to cultural customs as a sign of respect.

During her tenure as daytime talk show queen, Ellen DeGeneres was famed for getting her celebrity guests to dance awkwardly. In 2015, Michelle Obama appeared on "The Ellen DeGeneres Show" to promote her #GimmeFive dance challenge, which aimed to encourage people to embrace a healthier lifestyle. Obama's initiative already had the backing of Beyoncé, Nick Jonas, and the International Space Station, and this time it was her turn to get DeGeneres to bust some moves. Accordingly, she challenged the host to take part in #GimmeFive.

While Obama nailed the choreography, her outfit wasn't exactly ideal for the task at hand. The first lady wore a pair of white wide-legged trousers, which certainly weren't ideal for dancing, the hem grazing the floor. What's more, her microphone came undone as she danced energetically in the less than sporty attire.

Wide-legged white pants aren't the easiest look to pull off, with the statuesque Obama looking more elegant than most folks in the baggy garment. But she probably should have worn an outfit more suitable for a rigorous dance routine.

It's one thing to accidentally twin with someone at the same event, but twinning with a fictional character surely isn't a good look. In 2021, Kamala Harris inadvertently channeled Lisa Simpson's purple presidential ensemble during Joe Biden's inauguration. But she wasn't the first political figure to unwittingly take fashion inspo from a fictional character.

Six years earlier, Michelle Obama showed up to the State of the Union address in a gray suit that looked oddly familiar. As it turned out, she was sporting the same Michael Kors suit worn by "The Good Wife" protagonist Alicia Florrick. Evoking Florrick, a character who's the long suffering wife of a cheating lawyer-turned-politician, isn't exactly a message that a first lady would want to convey, particularly considering how loving Michelle and Barack Obama's marriage is IRL.

But Dan Lawson, costume designer for "The Good Wife," welcomed Obama's surreal sartorial choice. "I was watching the speech, and when [Michelle Obama] came walking out, my first thought was, 'Wow, she looks great, she always looks great,'" Lawson told the New York Post. "Then I realized, 'Oh, that's a Michael Kors suit. Wait a minute, I really know that Michael Kors suit. We used it on the show!'"

Since leaving the White House, Michelle Obama has showcased some flawless fashion moments. But not all of her post-FLOTUS looks have slayed. During the book tour for her memoir, "Becoming," in 2018, Obama paid a visit to the Para Los Niños Tina and Rick Caruso Early Education Center in Los Angeles, where she read to schoolchildren. But her outfit was mighty distracting.

Obama donned a double denim ensemble, paired with a white vest and tan pumps. It was an oddly Y2K get-up, evoking Britney Spears and Justin Timberlake's notorious twinning moment at the American Music Awards in 2001. This was the late 2010s, and thus several years before the Y2K resurgence, so Obama's outfit was hardly stylish for the time. Then again, perhaps she's a style innovator in more ways than initially thought, seemingly prophesying the aughts revival.

Look, it's hard to style denim on denim without looking like Britney and Justin, so we applaud Obama's effort. Was it a slay? Not quite. Did it make us nostalgic for flip phones and extremely low-rise jeans? You bet.

The 2024 Democratic National Convention served as an antidote to the vitriol that has come to encapsulate Donald Trump's increasingly toxic rallies. Sweetly, Barack and Michelle Obama engaged in some affectionate displays at the convention, with the former first lady introducing her husband as "America's 44th president and the love of my life." As a body language expert told us, the Obamas' PDA highlighted Melania Trump's major ick for Donald, with Barack and Michelle evidently maintaining a loving marriage throughout the years.

The convention was all about hope in the face of hate. As Michelle herself said (via the BBC), "Hope is making a comeback." But it's for this very reason that Michelle's outfit felt like a misfire to say the least. The former first lady wore a futuristic pantsuit from Monse's Resort 2025 collection, which took inspiration from aliens and AI. The sci-fi theme was incongruous with the event, particularly considering that Trump's 2024 campaign has been routinely described as a dystopian nightmare.

At a trendy luncheon, Michelle would have slayed in this fit. But at an uplifting political convention, it just felt distracting, evoking an eerie future that's the antithesis of her rousing message of positivity.