Michelle Obama — attorney, author, and former first lady — is a style icon for the ages. Her White House looks demonstrated her stunning transformation, but even the greats can get a look wrong sometimes. Yes, even Michelle has delivered a less-than-slay outfit on a few occasions. This isn’t about any kind of sartorial schadenfreude but rather taking comfort in the fact that someone as flawless as the former first lady can sometimes miss.
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Many of Michelle’s fashion faux pas were team mistakes. As Capricia Penavic Marshall, the chief of protocol for the United States from 2009 to 2013, told The New York Times, planning for the first lady’s clothing is a serious project: “No one just decides one day that this is what I’m going to wear.” Everything that Michelle wore had to be approved for political and cultural adherence. Even so, slipups happened.

In her memoir, “Becoming,” Michelle wrote of the style challenges she faced. “I tried to be somewhat unpredictable, to prevent anyone from ascribing any sort of message to what I wore. It was a thin line to walk” (via Elle).

Michelle Obama wore $540 shoes to a food bank

There’s casual, and then there’s first lady casual. As per a report from CBS News, Michelle Obama stepped out of the White House to volunteer at a food bank in Washington, D.C. in May of 2009, wearing a J. Crew argyle cardigan, khaki capri trousers, and a pair of $540 Lanvin sneakers. Dark grey suede topped with metallic pink toe caps and ribbon laces, the shoes are quite stylish and sold well during that spring’s season. They were even favored among other celebrities like Kanye West and Ellen DeGeneres. So, what was the problem?

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Some were quite angry that Obama wore such fancy sneakers to a food bank — as if she was flaunting her success and status. What did the first lady have to say about the controversy? According to the New York Daily News, her reps responded with, “They’re shoes.” Maggie Rodriguez from “The Early Show” quipped back, “But they’re expensive shoes.” Maybe Michelle Obama didn’t go quite casual enough.

Michelle Obama wore a sleeveless dress in her official White House portrait

While taking and distributing a first lady’s official White House portrait might seem like an old tradition to modern viewers, the custom only became official in 1961. According to Today, Mark Shaw’s photograph of Jackie Kennedy wasn’t originally taken in an official capacity, but it became so widely distributed that it is now regarded as her “official” portrait. Since then, every first lady has designated one photo to be her official image.

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Michelle Obama caused quite a stir, however, when she chose to go sleeveless in her first official White House photo. The picture depicts Obama standing next to a table in a sleek black shift dress and a classic pearl necklace. As per a report from ABC News, even though she looks stunning and elegant, some called out the first lady for being too informal. But Politico White House reporter Malika Henderson shared, “It is very much her signature look, so I wasn’t that surprised.” Perhaps the world just wasn’t ready for Obama’s amazing arms.

Michelle Obama exposed her arms at her husband’s State of the Union address

Michelle Obama’s official photo wasn’t the only time she went sleeveless: Obama exposed her arms at the State of the Union address in 2016, as per Time. And, according to The New York Times, the first lady also went sans-sleeves on a Vogue cover, when she spoke to the press regarding White House menus, and even when she attended her husband’s congressional address during his first year in office. What’s so wrong with Obama’s arms? ABC News declared it a mixture of informality and the fact that it was winter.

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Even though they’re controversial, no one can say that Mrs. Obama’s arms are anything but impressive. And they should be, considering she wakes up at the crack of dawn to lift weights several times a week. Wendy Donahue, a style reporter for the Chicago Tribune, told ABC News that no matter the controversy, Obama is “going to make bare arms her signature statement.” As she very well should.

Michelle Obama met the pope in a $2,290 dress

For some people, there’s no one more famous or important than the Pope, so it makes sense that Michelle Obama busted out her best dress when she met Pope Francis outside of Washington, D.C. in September of 2015. As reported by the Daily Mail, the first lady stepped out to greet the Pope outside of Andrews Air Force Base in a $2,300 Carolina Herrera dress in a lovely powder blue color. The dress also boasted a chic yet demure cowl neck and a flattering waist tie belt. Her daughters, Malia Obama and Sasha Obama, were also dressed to the nines in patterned graphic skirts and short sleeve black blouses.

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While the Obama family looked great, Pope Francis was probably not pleased with their expensive attire. His Holiness is well known for calling out capitalism and warning believers of the dangers of indulging in money. Whoops. Despite the conflicting messages, the Pope greeted Obama and her family with a warm smile. Perhaps even the Pope is good at being passive aggressive.

Michelle Obama wore short shorts

Who doesn’t wear shorts to cool off in the summer heat? Everyone does it. But, when you’re a first lady, people might not like it. That’s exactly what happened to Michelle Obama when she rocked short shorts back in August of 2009. According to Today, Mrs. Obama fell under fire for wearing a pair of grey shorts on a family vacation to the Grand Canyon. Though the shorts weren’t exactly risqué (they hit her mid-thigh), people felt that they weren’t an appropriate choice for a first lady riding on Air Force One.

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How did Obama herself feel about the controversy? In an interview she did with “106 & Park” on BET, Obama claimed that the grey shorts were her “biggest fashion regret” because they “created a huge stink.” However, it’s only the controversy she regrets, not the shorts themselves. After all, they were on vacation in the heat of the summer. Still, Obama did say that she wouldn’t wear shorts on Air Force One ever again.

Michelle Obama left her head uncovered in Saudi Arabia

The first lady has a lot on her plate, including balancing the complexities of official State appearances in other countries. That might be her toughest job, because each individual country Michelle Obama visited when she was the first lady had its own set of rules, customs, and preferences. And sometimes, the country’s official rules differed from their citizen’s preferences, like when the Obamas visited Saudi Arabia in January of 2015. As per a report from Time, Obama drew heat from Saudi Arabians because she didn’t wear a headscarf. People took to Twitter, posting angry comments like “Michelle Obama should’ve stayed in Air Force One as a sign of boycott rather than flouting rules of another country” with the hashtag “#Michelle_Obama_NotVeiled”.

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Even though people were mad, Obama hadn’t actually broken any rules. Time also reported that though women from foreign countries are required to wear demure, loose-fitting clothing while visiting Saudi Arabia, they’re not required to wear a headscarf. Poor Obama. She even got in trouble when she was following the rules!

She dressed too casually to meet the late Queen Elizabeth II

In 2009, then-President Barack Obama and First Lady Michelle Obama met Queen Elizabeth II and Prince Philip at Buckingham Palace. While everyone seemed to have a really nice time, Michelle was criticized for her choice of outfit. She wore a white blouse shirt, black cardigan, black skirt, black heels, and a double-strand pearl necklace.
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Several news outlets at the time, including HuffPost, lambasted the look. Michelle’s Alaïa cardigan was certainly a high-end garment, but critics felt like the combination of black and white was too lackluster. Even Oscar de la Renta weighed in on Michelle’s ensemble. “You don’t … go to Buckingham Palace in a sweater,” he said (via HuffPost).

During this visit, Michelle also courted controversy by touching the queen on the shoulder, breaking royal protocol. Years later, in “Becoming,” Michelle wrote about this moment and revealed that the two women were actually speaking about their outfits, particularly their uncomfortably tight shoes. “I then did what’s instinctive to me any time I feel connected to a new person, which is to express my feelings outwardly. I laid a hand affectionately across her shoulder,” Michelle wrote (via Harper’s Bazaar). Michelle continued, writing, “If I hadn’t done the proper thing at Buckingham Palace, I had at least done the human thing.”