Malia And Sasha Obama's Show Off Their Boldest Looks Yet In New Late-Night Photos

It's official: Malia and Sasha Obama are way cooler and more fashion-forward than 90% of America. 

Joking aside, we've watched the sisters grow up right in front of our eyes since their father, former President Barack Obama, took office in 2008. Over the years, we've seen both Malia and Sasha's personal styles evolve. When their father was first sworn in, Malia was 10 years old and Sasha was only 7, making her the youngest person to call the White House their home since JFK was in office.

At Barack's first inauguration in 2009, the Obama women made headlines for their somewhat unconventional attire, with Sasha donning orange and pink instead of the classic red, white, and blue. For their father's second inauguration ceremony, Malia and Sasha coordinated by wearing coats in different shades of purple. And when the sisters attended the White House state dinner for the first time in 2016, Glamour remarked how youthful and on-trend their styles were. For the formal event, Malia chose to skip out on any gaudy jewelry and Sasha wore a black choker with her formal dress.

Needless to say, the media has continued to keep an eye on the former presidential children. For instance, photos from the sisters' night out on the town could have more conservative dressers clutching their pearls, but the sisters certainly have fashionistas taking notes.

Malia Obama masterfully avoids print-clashing in two-print outfit

What do you wear to an after-party hosted by Drake? On August 22, Sasha and Malia Obama answered that question when they attended Drake's party after his concert in Los Angeles at the members-only restaurant, The Bird Streets Club. Paparazzi captured photos of the sisters as they exited the celebration and both of their outfits were absolutely on point for their personal styles. 

Harvard-graduate Malia sported microbraids along with a lace-up, sheer shirt with an amber, paisley-like print. If you were wondering, her top is from the SSense website (and unavailable, as of this writing). For bottoms, she donned semi-sheer, high-waisted, gray floral-print pants along with black platform shoes. While this may seem like an unconventional pairing on paper, the muted color scheme actually makes the paisley and flower prints blend to be cohesive and stylish.

Since leaving the White House, Malia graduated from Harvard University and is experimenting with working in film and TV with her latest job as a writer on Donald Glover's show, "Swarm." From overalls to baggy clothes to denim dresses paired with Marc Jacobs boots, the eldest daughter has developed her own eclectic style. Fashion magazine Highsnobiety noted in 2022 how the sisters have "mastered Gen Z style" by staying on-trend and even becoming trendsetters themselves.

Sasha Obama stuns in trendy corset top and oversized pants

While sister Malia Obama kept her outfit relatively minimalistic Sasha Obama went all out with her styling and jewelry for Drake's after-party. In a high ponytail, Sasha wore a black, semi-sheer, cropped corset top paired with oversized cargo pants. Accessory-wise, she donned hoop earrings, a chain necklace, and several colorful rings on her silver-manicured fingers. The youngest daughter finished her look with a fuchsia purse on her shoulder and black sandals.

After earning her degree in sociology from the University of Southern California in May, it's clear that Sasha has created her own fashion identity. For her everyday looks, her outfits tend to be bohemian-inspired with tie-dye, colorful patterns, and loose-fitting garments. Fashion publication Nss Magazine has already dubbed the former president's daughter as "the next style icon" for her "[realistic] way of dressing."

Even Drake himself has given Sasha props for her unique fashion sense. In 2017, the "Hotline Bling" rapper uploaded an Instagram photo (via Complex) of Sasha wearing a button-up shirt and one of his brand's hats. "Style popper," he simply captioned the post.

Parents Barack and Michelle Obama encourage free expression

While there have certainly been people who criticize Malia and Sasha Obama's fashion choices for being too risqué, their parents, Barack and Michelle Obama, have made an effort to foster confidence and individuality within their daughters. Proving their independence, Malia and Sasha moved to Los Angeles together in 2022 and became roommates. When discussing her parenting style on "Today" in 2022, Michelle emphasized that she tries not to have too much of "a critical eye" with her daughters.

In another 2022 interview on "The Kelly Clarkson Show" (via Entertainment Tonight), the former first lady revealed that she and Barack used to discourage their kids from getting tattoos but have since changed their tune. "Most kids who are wearing tattoos and piercings, they've got long nails, their value system is about individuality," she explained. "I'm grateful to this generation that is owning every part of themselves."

Barack spoke to InStyle in 2020 and commended Malia for her "[buoyancy]" and Sasha for her determination. "Sasha is ... completely confident about her own take on the world," he told the publication. "And is not cowed or intimidated — and never has been — by anybody's titles, anybody's credentials." With that kind of confidence, we're excited to see what's ahead for the Obama daughters' style evolutions.