Michelle Obama's Biggest Fashion Risks Of All Time

For the longest time, whenever the topic of fashionable First Ladies came up, there was only one name ever uttered: Jackie Kennedy. Even before she married JFK in 1953, Kennedy (née Bouvier) established herself as the pure embodiment of timeless sophistication among her fellow New York City socialites. While Kennedy was renowned for her style during her husband's presidency and for the rest of her life, eventually solidifying herself as a fashion icon, she would not be the only stylish First Lady to ever walk the halls of the White House.

Even before her husband was officially inaugurated in January 2009, future First Lady Michelle Obama brought her own sense of style to the table — not just in regards to fashion, but personality too. After eight years of Laura Bush and her conservative ways — both politically and style-wise — Obama wasn't just a breath of fresh air, but someone you knew from the start was going to do things her way. Over her eight years serving as First Lady, she never turned down the volume on who she was and is as a person. She simply exuded authenticity at every turn.

Because of her strong sense of self, Obama not only became an inspiration for future leaders everywhere, but a fashion icon too. She's taken a lot of fashion risks along the way — especially for a First Lady — but there are a handful that remain unforgettable.

During President Barack Obama's victory speech on November 4, 2008, Michelle rocked a fantastic red and black Narciso Rodriguez dress with a black cardigan. While not everyone liked the dress — because everyone's a critic — those in fashion knew the risky look was making a statement. And not just because red is the color of courage, strength, and passion. 

"That dress was unpretentious," fashion director of Barneys New York Julie Gilhart told The New York Times in 2008. "It said, 'Be who you are — don't let someone else tell you how to be.'" What was also cool about the dress choice was that it matched the rest of the family, as if to tell the American people the Obamas were united in doing what's going to be best for the country. Which is exactly what they did for eight years.

Look out, world! It's the First Lady in an off-the-shoulder black gown by Vera Wang. And what's that? A wee bit of cleavage? Oh, heck yeah; you go Queen! Obama wore a stunning custom-made dress for the 2015 White House State Dinner honoring Chinese president Xi Jinping and Madame Peng Liyuan.

While the dress itself would be deemed risky for a First Lady, there was a deeper meaning behind the choice: Vera Wang and her heritage. Although Wang was born in New York City, her parents were born in Shanghai. "It is such a privilege, as an American of Chinese heritage, to have dressed first lady Michelle Obama for this state dinner honoring President Xi Jinping and First Lady Peng Liyuan, of the People's Republic of China," Wang tweeted at the time (via Washington Post).

The thing about presidential inaugurations is that there are like 50 inaugural balls that follow them. Okay, so maybe that's a slight exaggeration, but there are a lot. However, it was the one-shouldered chiffon gown by Jason Wu that Obama wore to The Neighborhood Ball in Washington, D.C. that will always be memorable. Not only is the one-shoulder look risky in itself, but so was the choice of designer. Whereas First Ladies of the past might have gone with big name designers for such an event, Obama chose Jason Wu who, back in 2009 didn't have the name recognition that he has now.

Although the color white suggests new beginnings, the director of the Museum at the Fashion Institute of Technology Valerie Steele told The New York Times in 2013 that what Obama chooses to wear isn't about politics. "[Michelle] has been very strategic by sampling lots of different American designers and up-and-coming designers ... To make a pointed choice to choose Jason Wu both times doesn't sound to me like a political decision. It sounds like an emotional decision," said Steele, referencing the fact that Obama wore a second gown by Wu to another inaugural ball that same month. The white gown is now in the National Museum of American History.

If there's one fashion-related thing we can take away from Obama's time as FLOTUS, it's that the woman loves herself some J.Crew. While First Ladies of the past wore brands that most Americans couldn't afford, even when they weren't attending fancy state events, Michelle always kept it real. Although it's certainly not risky to wear something that fellow Americans might also wear, because our culture puts politicians (and their partners) on pedestals, it's almost expected that they would wear something superior, so to speak.

On October 27, 2008, just days before Barack would win the election, Obama appeared on "The Tonight Show With Jay Leno," where they spoke about clothes. (Leno was never one to talk about important stuff like Jon Stewart or Stephen Colbert do.) "I want to ask you about your wardrobe," Leno said after referencing the supposed $100k+ clothing budget of Sarah Palin, who was running as Senator John McCain's VP pick at the time. "I'm guessing about 60 grand? Sixty, 70 thousand for that outfit?" In response, Obama said, "Actually, this is a J.Crew ensemble. Ladies, we know J.Crew. You can get some good stuff online!"

Even after she officially became First Lady, she continued to wear J.Crew regularly. She's also probably the first and last FLOTUS to walk the White House halls in Chuck Taylors.

What does one wear when hosting Italian Prime Minister Matteo Renzi and Agnese Landini at their final state dinner? Versace, of course. The famous rose gold gown was beyond stunning, with Vogue calling it "the ultimate first lady mic drop," and it totally was. After eight years in the White House, Michelle Obama was going out with an absolute bang — and a bang that likely had Fox contributors clutching their pearls in horror.

While there were many articles and thought pieces that were written about the dress and what it represented, The New York Times' Vanessa Friedman put it best, "As much as it was gracefully cut and draped, it also spoke of armor and female strength, of the need to gird yourself to fight for what you believe in." That's what Michelle Obama always did and will continue to do in every corner of her life — not just fashion. It takes strength and courage to be your authentic self, but it's always a risk worth taking.