Malia And Sasha Obama's Head-Turning Transformations

Malia and Sasha Obama's head-turning transformations have been astonishing to watch throughout their years in the spotlight. 

Of course, the Obama sisters' lives will never be "normal."  After all, they spent their formative years living in the White House while their father, Barack Obama, served two consecutive terms as U.S. President. For Malia and Sasha, this meant going to school (and essentially everywhere else) with armed guards in tow, playing make believe surrounded by hundreds of years of American history, and eating family meals prepared by a full staff.

Still, the Obama sisters had an ace card. Their mother, Michelle Obama, ensured their childhood was as normal as possible during the eight years the family spent living at 1600 Pennsylvania Avenue. In the past, children of presidents have been the subject of tabloid gossip; however the Obamas were very strict about what was shared about their girls. Malia and Sasha were teenagers before the public knew anything about them, and both ladies have continued to retain an elegant distance from the media even upon entering college. What's more, the Obama sisters' flawless fashion moves only continue to impress. Here's a look at the head-turning transformations of Malia and Sasha Obama. 

Malia and Sasha Obama were brought into the world by IVF

Malia and Sasha Obama are presidential children who grew up to be gorgeous inside and out, thanks to the determination of their mother, Michelle Obama. 

Michelle detailed plenty of things fans never knew about Malia and Sasha in her memoir, "Becoming" — such as how she ultimately underwent IVF treatment in order to conceive both of her daughters."We were trying to get pregnant and it wasn't going well. We had one pregnancy test come back positive, which caused us both to forget every worry and swoon with joy, but a couple of weeks later I had a miscarriage, which left me physically uncomfortable and cratered any optimism we felt," she heartbreakingly recalled of her difficult path to motherhood. 

With her husband working full time, Michelle was left to inject herself with hormones, which she wrote about using to "manipulate" her body into getting pregnant. Thankfully, the incredibly stressful process was successful — and Barack and Michelle Obama eventually saw their dreams of having a family of their own come to life. 

Their sleepovers required armed guards

Malia and Sasha Obama's head-turning transformations were undoubtedly influenced by their time living in the White House — which, as one might imagine, offered many perks for the young sisters.

However, there were plenty of rules the presidential kids had to follow, as Michelle Obama told "CBS This Morning" host Gayle King during an interview at the 2019 Essence Festival. After all, the Obama sisters couldn't attend normal activities for kids their age — such as sleepovers — without having intimidating Secret Service agents in tow. 

As Michelle hilariously recalled to King, she would have to phone ahead to advise expectant parents that their personal details would need to be submitted in advance, and a sweep of their home would have to be carried out, too. According to the first lady, those phone calls would go something like, "Thank you for having Malia and Sasha over. Oh, by the way, there's gonna be a man with a gun sitting outside of your door all night." Michelle continued, joking, "Let him come in and use the bathroom. It would just be nice."

The Obama sisters were candid from an early age

Malia and Sasha Obama aren't exactly known to be presidential kids who live insanely lavish lives. Michelle Obama ensured her daughters' lives were as normal as they could be, constantly reminding them that their father's job had nothing to do with them. However, raising them to be normal kids — even in the midst of their father's historic presidential campaign — led to some funny family moments. As Michelle recalled in "Becoming," during an early interview with Access Hollywood, her daughters proved they knew how to lovingly embarrass their dad on national television. 

According to the former first lady, Malia — who was 10 years old at the time — spent the interview earnestly considering every question before answering, admitting her father did annoying stuff like trying to shake her friends' hands when they came over to play. Contrastingly, 7-year-old Sasha remained mostly nonplussed throughout the interview, interjecting only to enquire as to when they'd all be getting ice cream. However — as Michelle wrote in "Becoming" — in an especially hilarious moment toward the end of the interview, her youngest daughter gleefully exclaimed, "Daddy had an Afro once!"

They had to find normalcy in the White House

Growing up, Malia and Sasha Obama played pretend like other kids their age; however, their fantasies were quite obviously influenced by their lives as first daughters. For example, as Michelle Obama revealed to Gayle King during her aforementioned interview at Essence Festival 2019, her daughters' playtime would often include a wishful game of "pretend-those-armed-Secret-Service-agents-aren't-there."

In a 2018 interview with The Guardian, the former first lady admitted to initially having concerns about raising her daughters in the White House, saying, "I was extremely worried about raising our daughters in that environment, with butlers ready to bring them anything they wanted and photographers hoping to snap a picture of them any time they stepped foot outside the house," she recalled.

Thankfully, Malia and Sasha turned out to be far more resilient than their mother anticipated. As it turns out, the first daughters were far more interested in being regular kids than they were in the presidential trappings coloring their existence. According to Michelle Obama, Malia and Sasha had curfews, would make their own beds, and would help with household chores as needed — just like regular kids.

Their adventures across the globe helped shape their perspective ... for better or for worse

For Malia and Sasha Obama, getting to travel and experience different cultures undoubtedly contributed to their impressive transformations into well-rounded, intelligent adults. In "Becoming," Michelle Obama recalled a family trip to Rome, Italy — a memorable visit which an 8-year-old Sasha later wrote about for a school assignment. According to Michelle, Sasha nonchalantly noted in the assignment, "I went to Rome and I met the Pope. ... He was missing part of his thumb."

While speaking with Conan O'Brien during her book tour, the former first lady read the story about Sasha's school assignment to the audience (via On Milwaukee), using it as a way to showcase the sometimes mischievous, often hilarious nature of her daughters. However, as Michelle revealed, Sasha's school assignment also provided insight regarding her 8-year-old mindset. 

As Michelle realized, Sasha was small enough during the trip to Rome that she would have been standing at eye level with the Pope's thumb, and therefore was simply incapable of ignoring it. As the former first lady explained, this realization helped her see the anecdote as a gift rather than an embarrassing moment.

Malia and Sasha Obama handled dating and boys like total pros, thanks to their mom

While Malia and Sasha Obama certainly had a hard enough time making friends with Secret Service agents lurking behind them, one can only imagine how awkward dating must have been for the sisters.

"Imagine trying to have your first kiss [surrounded by] a bunch of men with [guns]," Michelle Obama quipped to Gayle King during her aforementioned 2019 interview. The former first lady acknowledged how difficult it was once the girls entered their teen years, saying that — aside from worrying about normal stuff like drinking and dating — she and Barack Obama knew the media was keeping on their family, too. "You had to worry about whether your kid was gonna wind up on Page Six," she recalled.

Fortunately, Malia and Sasha never ended up being known as presidential kids who got into weird relationships. As Barack Obama told the hosts of a North Carolina radio show in 2016, this was largely due to their mother (via Time). "She's such a great example of how she carries herself, [with] her self-esteem not depending on boys to validate how you look," he gushed about his wife.

Malia and Sasha Obama thrived at the White House with a little help from some famous friends

Malia and Sasha Obama's time in the White House was mostly happy for the sisters, thanks in no small part to Michelle Obama's commitment to keeping things as normal as possible. 

However, the former first lady also credits a handful of notable allies with keeping her daughters' heads clear while their father was running one of the most powerful governments in the world. During a 2018 appearance on "Good Morning America," Michelle gushed about how well her girls turned out and how proud she was of them, making sure to thank the famous ladies who assisted in her daughters' development.

"I will also say that they had support from a lot of the other former first kids, [such as] Jenna [Bush-Hager] and Barbara [Bush] and Chelsea [Clinton]," she said. Michelle continued, acknowledging how when anything bad was printed about her daughters in the press, other former first kids would jump to their defense. "Jenna would get in there and say something," Michelle revealed. "Chelsea would send a tweet out, and that made a big difference." 

Malia and Sasha Obama grew up to have quite the sense of humor

Malia and Sasha Obama generally steer clear of the public eye. However, some stories have inevitably come out about the sisters, leading fans to form pictures of who the girls are — to borrow a word from Michelle Obama — becoming. 

In 2018, when Barack Obama appeared on the first episode of David Letterman's Netflix talk show, the late-night legend shared a funny anecdote about the first time he met Obama's eldest daughter, Malia, at a party.

According to Harper's Bazaar's recap, Lettermen recounted the story of attending an event at the White House, during which he spotted Malia and headed over to introduce himself. "I go over, and I say, 'You don't know who I am. I know your mother and father. My name is Dave Letterman and I am very happy to be here at the party, and thank you for inviting me to the party," Letterman recalled. As he told the former president, Malia immediately delivered a hilariously sarcastic response, telling the late night legend, "Yeah, you look like a guy who really knows how to party." Fortunately, Letterman can take a joke.

Malia and Sasha Obama finally stepped outside of the presidential bubble

Malia and Sasha Obama never seemed as if they were presidential children who were troublemakers. So, as their eldest daughter started branching out on her own, Barack and Michelle Obama understandably loosened their reins around her and gave her their trust.

Of course, considering her parents had long been adamant that nothing be published about her in the media without their consent, Malia was somewhat of a mysterious public figure by the time she embarked on her college career. However, in 2017, she couldn't stay totally under the radar when Radar released photos and videos of her at Lollapalooza. 

Unlike other presidential children looking to present a pristine image, Malia took a gap year before entering college — something plenty of other "normal" kids her age had done (and continue to do). And while Malia herself hasn't stated her reasoning for doing so, perhaps the eldest Obama sister wanted to put some space between her life as a first kid and her life as an adult woman looking to make a life and career of her own.

Malia Obama made the transition to Harvard with her sister's help

While Malia and Sasha Obama may not have been quite as under the microscope when Malia entered the halls of Harvard in August 2017, the eldest Obama was still a noticeable newcomer. 

As noted in the Boston Globe (via Page Six), Malia didn't want to draw attention to herself. In fact, she even politely refused an interview from the publication when approached. And while Malia was recognizable amidst a sea of incoming freshmen, the Boston Globe noted how casually cool and normal she looked standing while standing around and chatting with fellow students.

As Barack Obama revealed in his 2018 interview with David Letterman, the whole family helped Malia move into her new college home. The former POTUS also told the late night legend that his youngest daughter tried to play it cool — although it was obvious she was going to miss her big sister very much. "[Sasha is] neater than her sister, so she was helping to make the bed and fold clothes, and just being really quiet about it but in a way that was really moving and touching," Obama recalled.

Malia Obama's move to Harvard was a transition for Sasha Obama as well

Considering Malia and Sasha Obama have always seemed to have a super close relationship, it's not surprising to hear that the youngest Obama sister was sad about her older sibling making the move to Harvard. However, as downtrodden as she might have been, Sasha apparently made a quick rebound. 

As Michelle Obama told Ellen DeGeneres in 2018, Malia being away at college meant Sasha scored the best bedroom in the family's first post-White House home. "She's got, like, a living room area and bedroom, and she designed it," Michelle revealed, noting the former president was mad he didn't get the best room.

According to Michelle, however, it was only fair for Sasha to get the best room. And while Barack might have a smaller room than he would have liked in his life after being president, Michelle joked to DeGeneres that Malia was the Obama with the short end of the stick. "She's got a room up in the attic somewhere," the former first lady said. She continued, joking, "She's away at college! You don't waste rooms on college kids."

The sisters have forged their own paths

By keeping Malia and Sasha Obama out of the spotlight during their White House tenure, Michelle Obama ensured nobody else would write her daughters' stories for them, or without their consent. However, with both young ladies college-aged and very much forging their own way in life, she took the opportunity to gush a little bit in a 2019 chat with Meghan Markle for British Vogue. In the interview, the former first lady noted the resiliency of her daughters, but said Malia and Sasha are otherwise total opposites. "One speaks freely and often, one opens up on her own terms," the doting mother shared. "One shares her innermost feelings, the other is content to let you figure it out."

Michelle was quick to note, however, that both ways of navigating the world are commendable. "Neither approach is better or worse, because they've both grown into smart, compassionate and independent young women, fully capable of paving their own paths," she said.

Malia and Sasha Obama's support for each other hasn't wavered

Malia and Sasha Obama are a sisterly dream team. When the time came for Sasha to head off to college, her big sis was naturally there to help with the move-in process. Speaking to Jenna Bush Hager on "Today" in 2019, Michelle Obama revealed that it was a tearful send-off as Malia handed her little sister off at the University of Michigan. However, according to the former first lady, the family cried less when dropping Sasha off than they did with Malia. "[We] didn't want to embarrass [Sasha] because, you know, she had roommates," Michelle revealed.

The family made an effort to keep major life events — such as dropping her kids off at college — as low key as possible. However, the Obamas did get emotional later that afternoon after saying their final goodbyes to Sasha."You feel a little melancholy that [your daughters] will never be the little ones that sit on your lap and listen to your every word and look at you adoringly," the former first lady said on "Today."

They are enjoying being independent women

For Malia and Sasha Obama, leaving for college was a major milestone. However, the uncharted territory of the college experience is full of highs, lows, and plenty of opportunities to learn from one's mistakes. And according to Michelle Obama, she wanted to make sure her girls tasted the real world without her watching over their shoulders. 

During an appearance on Oprah Winfrey's 2020 Vision: Your Life in Focus tour, Michelle revealed she follows neither Malia nor Sasha on social media and has no plans to do so (via People). The former first lady declared, "They have to walk their own walk. They cannot define themselves by looking at each other or looking at me or their dad."

According to the mother of two, she simply wants Malia and Sasha to have the breathing room to figure out who they are, to make mistakes, and to just be normal young women. "They have to take the time to get to know themselves. I don't want them measuring themselves by external influences, and for young girls that is hard to do," Michelle revealed.

Barack Obama is proud of his daughters for finding their voices

Former first lady Michelle Obama isn't the only one who admires how independent Sasha and Malia Obama have become. It should come as no surprise that their dear ol' dad, former President Barack Obama, also happens to be incredibly proud. "Sasha is, as Malia describes it, completely confident about her own take on the world and is not cowed or intimidated — and never has been — by anybody's titles, anybody's credentials," he told InStyle in 202 (via People). Moreover, Malia has been steadfast in her own point of view since she was a kid, with Barack recalling how the youngster refused to sample caviar when the family visited Russia, regardless of her parents' encouragement.

According to her dad, Malia is a "buoyant" person. "She's somebody who enjoys people, enjoys life, and enjoys conversation," he said. The Harvard grad is also apparently incapable of being bored. It's clear Barack is impressed with the young women his daughters have become.

Malia Obama scored a high-profile job with Donald Glover

After graduating from college, Malia Obama kicked off her own Hollywood career — although she didn't opt to be in the spotlight like her famous father. Instead, she chose to work behind the scenes as a writer. February 2021, The Hollywood Reporter confirmed the intrepid soon-to-be college grad had been tapped to join the staff of "Swarm," an Amazon Prime series spearheaded by Donald Glover. The "Atlanta" star, who executive produced the project, couldn't have been happier to have Malia on board. "She's just like, an amazingly talented person," Glover told Vanity Fair. "She's really focused, and she's working really hard."

The series, released in March 2023, follows a super fan (played by Dominique Fishback) obsessed with Ni'Jah, a Beyoncé-esque pop star (played by Nirine S. Brown). Malia worked on Episode 5 of the show, titled "Girl, Bye." Showrunner Janine Nabers gushed with praise for the First Daughter in an interview with ET. "Some of her pitches were wild as hell, and they were just so good and so funny. She's an incredible writer. She brought a lot to the table," she noted. "She's really, really dedicated to her craft." Fishback, who met Barack Obama's daughter while she was visiting the set, was also complimentary. "I think she's so intelligent. She's so cool. I just want to know what she wants to do next. Maybe we can do something together," she told E! News. We all have our fingers crossed.

Malia and Sasha Obama won't be following in their father's footsteps

Although their parents are both still heavily involved in public service, the Obama sisters probably won't be following in their footsteps any time soon. During an appearance on "The Late Late Show with James Corden," former President Barack Obama admitted Malia and Sasha Obama have too much history with politics to ever go into the "family business" themselves. "Them as teenagers having Secret Service guys follow them when they were going out on dates I think probably has shut down their interest in public service," he explained. 

Barack said, the girls, who entered the White House at the ages of 10 and 7 respectively, "still have PTSD from guys talking into their wrist microphones and glasses as they're trying to go to a music concert." However, the father of two acknowledged either daughter would be fully capable of handling the demands of being leader of the free world. "As a father, I want to protect my girls from that stuff," he said. "I think they are probably going to find other ways to serve rather than run for office themselves." Naturally, though, if either Malia or Sasha decides to run someday, their dad would be 100% behind them.

Malia and Sasha Obama got involved with the Black Lives Matter protests in 2020

The 2020 protests following the killing of George Floyd were a turning point for many people around the world. Citizens took to the streets, ready to make their opposition to police violence clear — including multiple celebrities. Malia and Sasha Obama were just two of the famous figures who chose to march.

In a November 2020 interview with People, former President Barack Obama shared that he was proud of his daughters for getting involved in activism even without his nudging. "I didn't have to give them a lot of advice because they had a very clear sense of what was right and what was wrong and [of] their own agency and the power of their voice and the need to participate," he said. "Malia and Sasha found their own way to get involved with the demonstrations and activism that you saw with young people this summer, without any prompting from Michelle and myself, on their own initiative."

Obama was especially happy to see that his daughters didn't seek attention for their efforts — they joined the protests subtly, wearing masks, simply because they believed it was the right thing to do. "They didn't do it in a way where they were looking for limelight. They were very much in organizer mode," he said. Even if Sasha and Malia choose not to pursue politics as a career, they're following their parents footsteps by making their stances known.

Sasha Obama transferred to USC and graduated with a sociology degree

After getting her start at the University of Michigan, Sasha Obama decided to finish her undergraduate education at the University of Southern California. She enrolled in USC's Dornsife College of Letters, Arts and Sciences, majoring in sociology. Both Barack Obama and Michelle Obama, plus Malia Obama, were in attendance at her May 2023 graduation ceremony, which took place on campus at Allyson Felix Field. Of course, they were also flanked by more than a dozen Secret Service agents, as noted in the Los Angeles Times.

When Sasha strode across the stage, wearing a mile-wide smile, the crowd erupted with applause. Her family ducked out of the ceremony after she received her diploma, not wanting to make a scene. Although the former president and former first lady didn't stop for photos, they radiated a friendly presence as they faced a horde of admirers: Michelle waved back at an excited onlooker, while Barack congratulated his fellow parents and relatives of graduates on his way out. Although Barack and Michelle didn't make any public remarks on Sasha's accomplishment, we can only imagine that they're immensely proud of her.

What kind of career will Sasha pursue with her degree? That remains to be seen — but with her family's support, she's sure to go far.

Malia and Sasha Obama live together in Los Angeles

In a 2022 appearance on "Today with Hoda & Jenna," former first lady Michelle Obama discussed her memoir "The Light We Carry" — and, in the process, opened up about Malia and Sasha Obama's lives. She revealed that they were not only best friends, but roommates, living life side by side in sunny Los Angeles. When the sisters invited their parents over for a cocktail night, both Michelle and Barack Obama were impressed by their homemaking skills — although Michelle joked that their martinis were a little weak. They wouldn't even let Michelle and Barack Obama put their martini glasses on the table without taking an important precaution first. "They were like, 'Uh-uh-uh, use a coaster,'" Michelle said. "And I'm like, you never used a coaster in my house!" That wasn't all — the girls even prepared a cheese board for their parents.

It seems that the sisters have been enjoying everything that Los Angeles has to offer — including its famously star-studded shindigs. In August 2023, Page Six noted they were spotted at an afterparty for Drake and 21 Savage's "It's A Blur" concert. The two showed up to the Bird Streets Club — a restaurant on Sunset Boulevard — in style, with Malia sporting a patterned ensemble and Sasha rocking a corset top with cargo pants. If the girls could survive the pressures of life in the White House, surely they can make it in Los Angeles' party scene.

Sasha Obama began her first romance in the public eye

During a 2022 appearance on "The Ellen DeGeneres Show," former first lady Michelle Obama revealed that Malia and Sasha Obama's dating lives had officially begun. "They loved the Jonas Brothers. Now they're bringing grown men home... Now they have boyfriends and real lives and all that stuff," she remarked. "They have grown up right before our very eyes and they are doing well."

Naturally, the interview piqued listeners' curiosity, and it wasn't long before the identity of Sasha's boyfriend was revealed by the Daily Mail. As the outlet noted in 2022, she'd begun dating Clifton Powell Jr., son of actor Clifton Powell. Clifton Powell Jr. was a basketball star during his college years; he now creates content for Nike and Peloton.

On a June 2022 episode of the "Dear Fathers Podcast," the elder Clifton Powell opened up about his son's relationship, sharing the advice he offered him. "They've been going out for about a year and it just hit the press," he said. "It has helped me talk to [him] about how to handle Sasha Obama because we love the Obamas, but Mr. Obama has a daughter that's dating my son, and I have an opportunity to make my son responsible, gentle, kind, loving, and supportive... I text him all the time, and I say, 'Treat Sasha like you would want somebody to treat your daughter.'" There haven't been many updates about the relationship or the pair's status since; evidently, Sasha's been able to keep her private life pretty private. 

Malia Obama's short film screened at Sundance

Film buffs might have noticed a first-time director named Malia Ann among the filmmakers making their Sundance debut in 2024. Turns out that this was none other than former first daughter Malia Obama, rebranding herself with a less attention-grabbing name. Her short, an 18-minute piece titled "The Heart," played as part of the Short Film Program during the festival.

Malia opened up about the project in a "Meet the Artist" video posted by the Sundance Institute. "This is an odd little story, somewhat of a fable, about a man grieving the death of his mother after she leaves him an unusual request in his will," she shared. An unusual request indeed: the film follows a gentle soul named Joshua (played by Tunde Adebimpe) who must carry around his mother's preserved heart in a jar after her untimely death. When he encounters a stranger who bears an uncanny resemblance to his mother, he has an epiphany about the healing process.

In the final moments of the video, Malia shared a message of gratitude. "The folks who came together to make this film have my heart, pun intended," she said. "I'm incredibly grateful to them for giving this story life, and we are grateful to Sundance for giving us the opportunity to share it with you all. We hope that you enjoy the film, and that it makes you feel a bit less lonely, or at least reminds you not to forget about the people who are."