Throughout American history, there’ve been several famous first ladies who became fashion icons. They set the standard for sartorial trends, elegance, and glamour. Naturally, the first name that comes to mind is Jackie Kennedy, who embodied the classic silhouettes of the ‘60s with aplomb. But in the 21st century, there’s been one former First Lady whose eight years at 1600 Pennsylvania Avenue really left a mark.
Former First Lady Michelle Obama has always matched her confident style with timeless cuts and a contemporary edge. Ever since we first met her on the campaign trail back in the late 2000s, we’ve been loving her fit and flare dresses, A-line gowns, and sleeveless looks. Her style has totally transformed since the late aughts, and while we’re sure she probably wouldn’t take all the credit for bringing back looks like high-waisted, wide-leg pants, her influence was likely instrumental in a few trends coming back into play.
But it goes without saying: we’ve loved seeing Michelle Obama’s style transform over the years. Regardless of what she’s fashioned for a formal or casual occasion, she’s always made it her own. Her looks consistently display a timeless quality coupled with a fierce modern aesthetic. But her best accessory with every one of these looks? The confidence with which she carries herself.
Take a look through our round-up featuring Michelle Obama’s style evolution from the campaign trail in 2008 all the way to the January 2021 inauguration.
January 2008
Let’s take it all the way back to the beginning: we first met Michelle Obama on the campaign trail in 2008 when her husband, President Barack Obama, was running for office. The couple made a number of stops throughout the country, including this January 2008 trip to New Hampshire. Given the cold temperatures, Mrs. Obama opted for a classic black turtleneck, with a high-waisted pencil skirt and a pearl necklace. It may have been 2008, but with this classic outfit we wouldn’t have any idea!
February 2008
The next month, the Obamas went back home to Chicago for Super Tuesday. Since February is the month of Valentine’s Day, we can’t help but think that influenced Mrs. Obama’s stunning red dress and matching jacket.
April 2008
After sharing the stage with her husband, Mrs. Obama took the mic herself during their stop in Pittsburgh in April 2008. While there, Mrs. Obama showed us her love of high-waisted, wide-leg trousers. She paired this look with a red shirt, black cardigan, and detailing around her waist.
August 2008
One of the former first lady’s most memorable looks came at the Democratic National Convention in August 2008. While standing on stage with her daughters, Sasha and Malia, Mrs. Obama sported this turquoise dress. It was simple, elegant, and totally timeless.
November 2008
Mrs. Obama wore another memorable look the night she and her family found out her husband was the next President-elect. This stunning Narciso Rodriguez sheath dress with a black cardigan was so lovely, and complemented what each member of her family was wearing, too.
January 2009
Look at those smiles! During the Inauguration Parade, Mrs. Obama joined her husband to greet citizens. She dazzled in this Isabel Toledo dress and coat. Honestly, you could wear this today!
Inauguration Ball 2009
Want to join us in swooning over this gown? Michelle Obama wore this Jason Wu formal dress with floral detailing to the 2009 Inauguration Ball in Washington D.C. in December 2009. While the one-shoulder look may have been trendy at this point, Mrs. Obama still pulled it off and gave it her own classic spin.
Easter 2009
Now, we’ve gone through quite a few formal and business looks that Mrs. Obama wore during those first few months the world got to know her. But once she was the First Lady of the United States, we got to see what Mrs. Obama’s casual style was like. She wore this look during the 2009 Easter Egg Roll at the White House and looked fashionable, but also totally comfortable.
April 2009
During an event in the Rose Garden in April 2009, Mrs. Obama showed off one of our favorite trends she rocked throughout her husband’s presidency. We loved this fit and flare dress with a belted waist. She looked classic and comfortable.
June 2009
For one of the Obamas first trips overseas, it seemed like Mrs. Obama coordinated with a fellow first lady. She wore this white dress with a belted waist during their trip to France in June 2009.
July 2009
Now, while we know Mrs. Obama was and remains an incredible partner for President Obama, she also can carry her own. During the National Design Awards in July 2009, Mrs. Obama slayed us in this yellow tweed look with large buttons. We like to think this look was a combo of Jackie O. elegance and Michelle O. effervescence.
August 2009
Of course, the Obamas did a lot of traveling, too. But everytime she stepped off Air Force One, Mrs. Obama always looked so elegant. She wore this fit and falre dress in August 2009. Again, take note, this is another look you can easily rock today!
September 2009
While Mrs. Obama clearly loves a classic silhouette, even she took some fashion risks. This dress was worn in Pittsburgh during the G-20 summit. She paired the dress with a string of elegant pearls.
Joint Session of Congress, September 2009
Fashion risks aside, you can never go wrong with a classic cut. The former First Lady of the United States looked simply marvelous in this soft magenta look during President Obama’s Joint Session of Congress address. Although there were a number of distinguished guests, Mrs. Obama totally stood out.
January 2010
If there’s one thing we’ve come to know and love about Michelle Obama, it’s that she can be all business. Back in January 2010, she even rocked a business bob with this fitted gray look. Commander in Chief, meet the Commander in Fashion.
May 2010
From business to something a little more playful, Michelle Obama has never been averse to working a pop of color. She did just that on May 5, 2010 during a celebration of Cinco de Mayo in the Rose Garden.
September 2010
Another gown! Another gorgeous gown! Listen, we love Michelle Obama in a gown — heck, we love ourselves in one, too. But she absolutely slayed in this red sleeveless gown at the Congressional Black Caucus Foundation Inc.’s Annual Legislative Conference Phoenix Awards Dinner at the Washington Convention Center in September 2010.
January 2011
So, as we previously discussed, we know that red is a fabulous color on Michelle Obama. But this gown worn during a state dinner at the White House with China’s President Hu Jintao in January 2011, was just on a whole different level. The orange-red Alexander McQueen gown featured an asymetrical neckline and inspired use of floral print.
November 2011
Another look Mrs. Obama wore while disembarking Air Force One was this simple and timeless gray and black ensemble. With a gray top, matching skirt and jacket, black knee-high boots, and a statement necklace, Mrs. Obama looked so elegant.
February 2012
We’ve always loved how much Mrs. Obama embraced ’50s and ’60s flair in nearly everything she wore. This patterned look was one of our favorites, worn during the groundbreaking ceremony for the construction site of the Smithsonian National Museum of African American History and Culture in Washington in February 2012.
January 2013
Now, we don’t want to play favorites, but if we had to choose between the 2009 Inauguration Ball gown Mrs. Obama wore and the 2013 gown, we’d definitely go with this dress by Jason Wu. Again, red is definitely Mrs. Obama’s color, and this dress shows why.
March 2014
Remember that black and gray lace look Mrs. Obama sported off of Air Force One? Well when something works, make it as versatile as possible. That’s exactly what Mrs. Obama did during the Builing a Healthier Future Summin in March 2014 with this fit and flare dress with a bold belt across the waist.
February 2015
In February 2015, the former first lady made business look so chic with her attire at the Celebrating Women of the Movement” event. She paired this white dress shirt with a gray skir and metallic belt.
April 2016
During the Obamas last year of duties, they made the trip across the pond for a visit with the royal family. Here, Mrs. Obama clearly stands out with her modern, A-line coat and monochromatic ensemble.
May 2016
Want to swoon with us again? Goodness, this dress worn by Michelle Obama for the state dinner with Nordic Leaders was breathtaking. The blush gown was designed by Naeem Khan and featured an asymetrical neckline and one-shoulder sleeve.
January 2017
This was a totally different Michelle Obama than we’d seen before. At the 2017 inauguration, Mrs. Obama wore a Jason Wu coatdress with a slicked back bun.
May 2018
Out of the White House, Mrs. Obama really embraced her casual style. I mean, we’re sure she loved the gowns, but it’s nice to wear just a jean jacket from time to time, right?
April 2019
While promoting her book Becoming in April 2019, Mrs. Obama embraced more modern trends, including metallics, which we’d seen her wear before, but never like this!
August 2020
Sadly, due to the pandemic, we didn’t see a lot of the Obamas, which meant a lot less of seeing Mrs. Obama’s incredible style. But during the 2020 DNC in August 2020, she broke out this mocha look with a necklace that said “vote.”
January 2021
At the 2021 Inauguration, it felt like the former first lady was ready to turn the place into her own runway. This look designed by Sergio Hudson was absolutely show-stopping. With the monochromatic plum color, the high-waisted pants, and bold belt, this was one of Mrs. Obama’s best looks yet.
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