Michelle Obama's Style Evolution Since Leaving The White House

Even before former First Lady Michelle Obama left the White House, she was serving up looks that no other First Lady in history had even dreamed to attempt. As a natural fashion risk taker, Obama never played by the rules when it came to her sartorial choices, proving that right up to her final state dinner at the White House in 2016 when she flawlessly pulled off a strapless, rose gold gown by Atelier Versace.
The full-length custom gown (which was made entirely of chain mail) left a lasting impression on audiences. The New York Times interpreted it as a message about women's resilience through every obstacle.

Following those years in the White House, Obama's style has remained a topic of conversation. And it's easy to see why. For fans, getting to see Obama shine without the constraints of politics has been a lot of fun to watch. Not only are her outfits consistently put-together, but they also serve as inspo for young professional women everywhere. That's in part thanks to the work of professional stylist, Meredith Koop, who has been dressing Obama for over a decade. To this day, Koop and Obama continue to work together, with the stylist telling Vogue in 2022 that styling the former First Lady requires her to "block out certain things." In any case, Michelle Obama is proof that with the right attitude and confidence, you can literally wear anything and make it look like it was made specifically for you.

In December 2023, Obama attended the American Symphony New Orleans Premiere rocking, of all things, a leather jacket and large hoop earrings. But the most important part of her look was her natural hair. Realizing that Americans "weren't ready" for her natural hair, Obama made the decision to straighten it. "Let me keep my hair straight," Obama told The Washington Post in 2022. "Let's get healthcare passed." 

During her appearance on Revolt that same year, Obama continued the hair conversation. "We were the first. And I was like, first of all, they've got to get used to us," Obama said. "When we did a fist bump with each other, they turned that into a terrorist act. Who needs the hassle?" Because of this, she opted for straighteners and blowouts, and used extensions and other tools to protect her natural hair from damage. 

In addition to embracing her natural hair once she was free of the White House, it became very clear that Michelle Obama loves anything that shimmers. Even before sequins became huge in 2024, Obama wore a lot of eye-catching, glitzy outfits. In July 2019, she stole the show  at the 2019 Essence Festival in a navy blue sequin jumpsuit by designer Sergio Hudson. Complete with a large belt and thin strap heels, the look 

What happens when you put two fashion icons in one building at the same time? In some cases, magic occurs. But in the case of Michelle Obama and Sarah Jessica Parker, it was more on par with a star being born in the universe and emanating light in all directions! And this is, in no way, an exaggeration. While doing the promo rounds for her memoir, "Becoming," Obama sat down for a chat with SJP at the Barclays Center in December 2018.

Although Parker kept things fairly demure (and mindful), as opposed to her "SATC" character Carrie Bradshaw, Obama pulled out all the stops. Not only did she opt for a yellow wrap dress by Balenciaga, but she completed the outfit with shimmery, thigh-high boots also by the Spanish fashion house. The boots, in case you were thinking about getting a pair of your own, were a whopping $4,000 and something that probably ruffled the feathers of Republicans despite the fact that Obama was no longer First Lady. When the boots came up in conversation, Obama told Parker, "Now, I'm free to do whatever [and] they were just really cute," said Obama. "I was like, 'Those some nice boots!'"

When Obama showed up to the "When We All Vote Rally" at Watsco Center at the University of Miami in September 2018, she kept things super casual. So casual, in fact, that her jeans had — gasp! — rips in them. Jeans have long been associated with the American counter culture, like James Dean in the 1950s and hippies in the 1960s and 1970s, to see a former First Lady in ripped jeans is a sight to behold. Granted, they were trendy, but considering that her casual outfits during her First Lady days typically consisted fit-and-flare midi dresses, or skinny jeans and closed-toed shoes, the relaxed fit denim and sandals were indicative of a clear shift in her styling. It says that she's not only comfortable in her skin, she knows her audience, and she doesn't see herself as being elite or better than anyone else.

Often affectionately called the Canadian tuxedo, denim-on-denim has come a long way since the early aughts. But if you carry yourself with confidence, it's easy to pull off — a fact a fashion icon like Michelle Obama knows very well. While promoting her book, "The Light We Carry: Overcoming in Uncertain Times," at the Warner Theater in Washington D.C. back in November 2022, the former First Lady walked out on the stage in a ridiculously cool-looking head-to-toe denim by Ganni. The two piece set featured a looser fit and extra-large pockets on the sides, giving off an effortlessly confident vibe that commanded power while remaining totally relaxed. It felt like a natural evolution from the colorful
jumpsuits  and pajama-inspired fashion we saw her wear during the 2018 press tour for her book "Becoming."

Obama completed her outfit with a pair of Stuart Weitzman boots and, as she has pretty much done most of the time since leaving the White House, she wore her natural. Sure, she wowed the crowd while talking about her book, but we'd be remiss to say her look didn't equally wow the audience.