Michelle Obama’s Most Shockingly Inappropriate Outfits

Compared to women like Melania Trump, Michelle Obama was one of the most modest and unassuming First Ladies in United States history. And they each made history in their own ways. Michelle was the first Black FLOTUS, and Melania was the first FLOTUS that had posed nude for the world to see.

In other words, Michelle Obama rarely did anything that was ever as inappropriate as her successor, but she still found ways to shock people, especially when it came to her wardrobe. In fact, some of her outfits were so shockingly inappropriate that they created the worst kinds of buzz, and we are still discussing those outfits to this day.

What are the most inappropriate outfits ever worn by Michelle Obama? Keep reading to find out!

Uncovering her head in Saudi Arabia

It doesn’t take long to learn that what is and is not inappropriate is dependent on certain contexts or cultures. Basically, what is perfectly appropriate here may not be appropriate somewhere else.

That’s something Michelle Obama discovered when she visited Saudi Arabia in 2015. When doing so, she decided against wearing a headscarf, which is the conservative cultural requirement of most women in that area.

Here’s where it gets interesting: as a visitor from a foreign country, she was never expected to wear a headscarf, but many felt she should have obeyed more of the local customs, including the headscarf, to show respect, and the whole thing turned into a weird online controversy. 

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Going all-out for the Pope

Part of being First Lady meant meeting important dignitaries from all around the world. It is perhaps ironic that when Michelle Obama met the Pope, she learned the real meaning of the old phrase “damned if you do, damned if you don’t.”

In order to show Pope Francis the respect he is due, Michelle went all out and ended up buying a stunning blue Carolina Herrera dress that cost $2,300. Nobody can deny that she looked quite stunning in the dress, but it’s important to note that Francis had been very vocal about the evils of capitalism as well as the dangers of spending too much money. To a man with those beliefs, greeting him in a dress that costs thousands of dollars is as good as slapping his face.

The infamous sleeveless portrait

Since Jackie Kennedy kicked it off in 1961, it has become customary for every First Lady to have her own White House portrait. Michelle Obama could have worn anything for her own official portrait, but what she chose to wear caused a minor controversy that, in many ways, never really cooled down.

Specifically, she wore a sleeveless dress and a pearl necklace. It is, frankly, a timeless look, and it may very well have helped capture the timeless grace of Obama herself. However, some critics said that her outfit was too informal for such a portrait. Then again, considering her love of sleeveless looks (more on this later), we’re not sure what Michelle Obama’s haters thought she was actually going to wear.

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Flexing at the food bank

Remember when we talked about “damned if you do, damned if you don’t?” Well, Michelle Obama got another dose of that when she volunteered at a Washington, D.C. food bank back in May 2009.

There were other celebs there, including Ellen DeGeneres and Kanye West, so if Michelle Obama skipped, it might have looked like she didn’t care about the poor people visiting the food bank. So she didn’t just show up, but she showed up in style, including a pair of Lanvin sneakers that cost $450. Michelle didn’t think anything of it, but many thought wearing shoes worth nearly half a grand to serve food to poor people was nothing more than a mean-spirited flex.

Shocking exposure at the State of the Union

Somewhere along the way, “sleeveless” became Michelle Obama’s signature look despite (or perhaps even because of) how many noses it put out of joint. Therefore, it wasn’t very surprising when she showed up to Barack Obama’s 2016 State of the Union speech in a sleeveless yellow dress.

However, something can be shocking even when it’s not that surprising. In this case, Obama got the usual round of criticism due to dressing too informally for such a major event. Some fashion snobs also felt yellow was a strange color to wear in the middle of winter. However, Michelle Obama got the last laugh by not only wearing a sleeveless, out-of-season dress but looking great while she was doing it.

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Michelle’s short shorts

While most critics of Michelle Obama stick to complaining about what she wore to official events, some take it a step further and complain about what she wore on vacation. And no item of clothing ended up causing more of a stir than the short shorts that she wore on a family vacation to the Grand Canyon.

It may have been a family vacation, but it didn’t take long for photos to leak of Michelle wearing short (but not that short) shorts on the trip. This caused many to say that she shouldn’t be wearing something so informal while traveling on Air Force One. Interestingly, Michelle ended up agreeing, saying in an interview with 106 & Park that these shorts were her “biggest fashion regret.” And after this silly controversy, she vowed to never rock shorts aboard Air Force One again!