In many ways, Michelle Obama’s brand is even stronger than Barack Obama’s. The mere mention of her name conjures the image of a kind woman with poise, grace, and modest outfits.
But Michelle is more than capable of surprising you. Sometimes, the outfits go past “modest” and into “scandalous.” And if you don’t believe it, we’ve assembled the most scandalous outfits ever worn by Michelle Obama!
White House portrait dress
When we discuss Michelle Obama outfits that raised eyebrows, one of the wildest moments happened early on in her time as first lady, in her official White House portrait in 2009.
Since 1961, photos of first ladies have been taken to create their official White House portrait. The choice of outfit is very important here: in a very real way, all of these women are participating in a historic moment for the nation.
And that is why Michelle Obama’s decision to sport a sleeveless dress was so shocking. The photo caused an instant stir across the various political aisles. Some thought she was dressed too informally for such a major moment. Others simply admired her amazing arms!
Whether they loved her or hated her, nobody was quite ready to see Michelle in that killer dress. Or maybe they just weren’t ready for a first lady with toned arms.
Meeting the pope in a $2,290 dress
A major part of being the first lady is going on official trips and meeting some very important people. And one of the most important people that Michelle Obama and her family ever met was Pope Francis in September 2015.
Presumably because he is such an important person, Michelle went “all out” for her outfit. She wore a powder blue Carolina Herrera dress that costs a hefty $2,290. Of course, the fact that she wore an expensive dress isn’t the entire reason that this outfit was a bit scandalous.
The main reason is that Pope Francis has taken particular aim at the dangers of capitalism and the dangers of loving money too much. And it has been reported that he often disguises himself so that he can minister to the homeless.
So, wearing such an expensive outfit to meet the pope might have come across as a bit tone deaf.
Then again, it was nowhere near as scandalous as the next outfit.
The short shorts
At some point, you have to feel pretty sympathetic to Michelle Obama. When it comes to her fashion choices and potential scandals, there are times when she just can’t win.
The best example of this is when Michelle and her family took a summer vacation to the Grand Canyon in August 2009. In order to beat the heat, she made the logical decision to wear some shorts.
However, the shorts were a little shorter than some people were ready for. Soon, the fact that Michelle rocked some short shorts was the talk of the nation. It got bad enough that Michelle later said on 106 & Park that these shorts were her “biggest fashion regret.”
“Sometimes I forget I’m the first lady and I’m running around in shorts,” she said. “It created a huge stink because people were like, ‘She’s wearing shorts getting off of Air Force One.'”
She defended the choice as just something she was wearing for vacation. But after the scandal, she never wore shorts on Air Force One again!
Sporting $540 shoes to a food bank
By now, you’ve probably figured out the real source of most of these fashion scandals. It’s not usually that Michelle Obama is dressing overly risque. Instead, she is failing to “read the room,” and this can lead to disastrous results.
For example, look at what happened when Michelle Obama volunteered at a food bank in Washington, D.C. in May 2009. Her action was certainly laudable, and we wish that more public servants actually took the time to serve the people so directly.
A scandal happened, though, because Michelle was wearing a pair of $540 Lanvin sneakers. It led to many people believing she was flaunting her wealth or simply turning her time at the food bank into a photo opportunity for herself.
But was that really any worse than the next choice of outfit?
Sleeveless at the State of the Union
It’s the scandal so nice she caused it twice!
Michelle Obama’s sleeveless White House portrait photo caused a stir across the nation. But she caused a similar scandal when she wore a mango-colored sleeveless dress for the 2016 State of the Union address.
The public was split on claiming that she was being too informal for such a major event and admiring her toned arms.
However, by wearing a dress by Cuban-American designer Narciso Rodriguez, The New York Times noted that the fashion statement was deliberate. The publication called it a “nod to the resumption of diplomatic relations between the countries that is part of her husband’s legacy.”
And can you really consider a dress originally priced at $2,290 as “informal”?
Uncovered head in Saudi Arabia
Obviously, the idea of what is scandalous depends greatly on context. What might be perfectly normal in one part of the world may lead to major controversies in other parts.
We can see this on full display when Michelle Obama visited Saudi Arabia in January 2015. Most of her clothing was completely modest (no bare arms or short shorts to worry about here). However, she neglected to wear a headscarf with the rest of the outfit.
In the U.S., that would be no big deal at all. But this caused a major controversy among the Saudi Arabians she was visiting, with some going so far as to say she was deliberately flouting the rules and customs of a foreign country right to their faces!
The Smithsonian portrait dress
Can you see a running theme of why people freaked out about Michelle Obama outfits? Clearly her decision to wear sleeveless dresses just doesn’t sit right with some people to this day.
Take the sleeveless Milly dress Michelle wore for a portrait commissioned by The Smithsonian’s National Portrait Gallery in 2018 and painted by artist Amy Sherald.
“It’s up to Mrs. Obama to say why she chose this for the portrait, but I would say that it’s a very modern, emotional dress with a very womanly, very American spirit,” designer Michelle Smith of label Milly told Vogue when the portrait was revealed.
“The dress also reveals her arms, which I believe is groundbreaking and very modern for a portrait of the first lady.”
She summed up, “Her portrait represents her perfectly — her intelligence, modernity, confidence, sensuality, and kindness. It’s a very open, honest, and beautiful portrayal of her.”