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The Stunning Transformation Of The Obama Sisters

February 2, 2023
During their dad's two terms in the White House, "first kids" Sasha and Malia Obama have transformed from cute tweens to sophisticated fashion icons right before our eyes. Let's take a look back at some of the greatest moments in sister style. 
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When The Obama Sisters Stepped Out At The Democratic National Convention

When the Obama sisters stepped out at the Democratic National Convention 1
When the Obama sisters stepped out at the Democratic National Convention

The future first family looked perfectly put together in rich magenta hues at the 2008 Democratic National Convention. This event marked the beginning of the Obama family's presidential journey. At the time, Sasha and Malia were just 7 and 10 years old, respectively, yet they already exhibited the style and grace of seasoned political pros.

The Obama Sisters Made A Colorful Crew On Inauguration Day

The Obama sisters made a colorful crew on Inauguration Day 2
The Obama sisters made a colorful crew on Inauguration Day

For Barack Obama's first presidential inauguration in January 2009, the Obama sisters stepped out in colorful wool coats and winter accessories designed especially for them by J.Crew. Malia, 10, looked stunning in sapphire blue, while Sasha, 7, appeared age-appropriate in tones of orange and pink. Over the years, the first lady and her daughters have frequently turned to this iconic American brand for classic statement pieces.

Following the inauguration, J. Crew stocks jumped 10 percent, reported The New York Times, and its web site temporarily crashed due to the overwhelming volume of traffic looking to mimic the first family's style. 

And Puppy Makes Five

And puppy makes five 3
And puppy makes five

In April 2009, the White House announced that the Obama family had accepted a gift from Sen. Ted Kennedy, a Portuguese water dog named Bo. Here are Sasha and Malia getting to know Bo—and the strength of his leash—on the South Lawn of the White House on April 14, 2009. The puppy's photo op also gave the nation a chance to see the girls dressed casually, just like any other kids.

The Obama Sisters' Sunday Best

The Obama sisters' Sunday best 4
The Obama sisters' Sunday best

Nearly two years into Obama's first term, 9-year-old Sasha and 12-year-old Malia continued to epitomize elegance in and around Washington D.C. Notice the sibling sophistication during this visit to St. John's Episcopal Church, known as the "Church of the Presidents" on September 19, 2010.

The Obama Sisters Went Jet Setting In Style

The Obama sisters went jet-setting in style 5
The Obama sisters went jet-setting in style

When your father is President of the United States, you're inevitably going to do some world traveling. The adorable tweens donned patriotic patterns to meet Brazilian President Dilma Rousseff at Palacio do Alvorada in March 2011.

Christmas In Washington For The Obamas

Christmas in Washington for the Obamas 6
Christmas in Washington for the Obamas

The Obama sisters dazzled on stage in 2011 for the 30th annual Christmas in Washington concert held at the National Building Museum. Joined by plenty of music celebrities, including Justin Bieber, Jennifer Hudson, and Cee Lo Green, Sasha and Malia stood out from this A-list lineup in stunning holiday frocks. Malia, 13, looked all grown up in a mustard yellow satin dress with bell sleeves by Elizabeth and James, and Sasha, 10, appeared lovely in lavender.

The Obama Sisters Looked Like A Million Bucks...on A Budget

The Obama sisters looked like a million bucks...on a budget 7
The Obama sisters looked like a million bucks...on a budget

When you're as powerful as the Obama family, one would assume the price tag of the kids' wardrobes would be the equivalent of a year's worth of rent. Well, think again. The first daughters have routinely proved that you don't need to spend a lot to look like a million bucks. A classic example of this: the family's trip to the Nickelodeon 25th Annual Kids' Choice Awards in March 2012. Sasha and Malia donned affordable and chic ensembles by U.K. online shopping brand ASOS. According to NBC News, Malia's leather belt retailed for about $36 and Sasha's mono print dress cost about $75.

Where Did The Time Go?

Where did the time go? 8
Where did the time go?

Sasha and Malia had everyone asking, "Where does the time go?" when they appeared at the 2012 Democratic National Convention looking poised and oh so sophisticated. Gone were the doll-like pink dresses of their first inauguration. For this occasion, Malia, 14, continued to prove she is the spitting image of her mother in a chic blue dress by H&M and nude ballet flats. Sasha solidified her standing as the most fashionable 11-year-old in the world in a printed dress by Anthropologie, paired with a studded yellow belt and silver flats.

The Obama Sisters Were A Polished Pair On Their Second Inauguration Day

The Obama sisters were a polished pair on their second Inauguration Day 9
The Obama sisters were a polished pair on their second Inauguration Day

At the start of President Obama's second term in office, it was remarkable to witness just how much the first daughters had grown up in four short years. Entering the inaugural ceremony in complementary coats, Malia wore J.Crew while Sasha opted for Kate Spade. The two looked incredibly mature, but when they pulled out a cell phone for obligatory selfies, these two proved that no matter how grown up they looked, they were still just kids.

Totally In Demand

Totally in demand 10
Totally in demand

Need more proof that Sasha and Malia are trendsetters? Sasha, 12, created such a frenzy after she donned this $18 unicorn sweater from ASOS to a college basketball game, that fans actually contacted the company demanding the sweater be reissued. Now, that's what the fashion industry would call a slam dunk.

The Obama Sisters Displayed Fashion Forward Diplomacy In China

The Obama sisters displayed fashion-forward diplomacy in China 11
The Obama sisters displayed fashion-forward diplomacy in China

On a trip to China to visit President Xi Jinping and his wife Peng Liyuan, the Obama ladies stunned in shades of red. Twelve-year-old Sasha's crimson dress was cute and flattering next to her mother's outfit, but 15-year-old Malia's pick snagged all the headlines. The New York Daily News called the $112 two-tiered floral pattern from Topshop "the frock heard round the world." It reportedly sold out of stores soon after photos of the young lady emerged.

A Velvet Vision And A LBD

A velvet vision and a LBD 12
A velvet vision and a LBD
In 2014, Sasha and Malia once again stole the show at the annual Christmas in Washington event, each donning age-appropriate holiday dresses that walked the fine line between fun and tradition; girls and women. Malia, 16, wore a little black dress with floral tights and Sasha,13, choose a burgundy velvet piece as they met with former patients of the Children's National Health System.

Che Bello! The Obama Sisters Look Lovely In Italy

Che bello! The Obama sisters look lovely in Italy 13
Che bello! The Obama sisters look lovely in Italy
Summer 2015 was a season packed with travel for the Obama ladies. Arriving in Milan, Italy in June with their mother, Sasha and Malia both sported a chic and effortless sundress style. Sasha, 14, who is almost as tall as her 5-foot-11-inch mother, picked a seersucker dress by American Apparel and a pair of leather gladiator sandals, while Malia, 16, flaunted a simple gray heathered dress.

Giving Thanks For Dad Jokes And Stylish Looks

Giving thanks for dad jokes and stylish looks 14
Giving thanks for dad jokes and stylish looks
In November 2015, Sasha and Malia looked terrifically trendy as they stood by their dad's side during the White House's annual turkey pardoning ceremony. Sasha, 14, rocked an American Apparel sweater-jean skirt combo paired with studious glasses. Malia, 17, also donned an American Apparel top under a color-blocked jacket, with leggings and boots. The best part of these outfits? Both girls accessorized with big grins while enduring what appears to be a classic "dad joke."

Sophistication At The State Dinner

Sophistication at the state dinner 15
Sophistication at the state dinner
In March 2016, Malia and Sasha Obama attended their first state dinner at the White House wearing embroidered Naeem Khan gowns worth nearly $20,000 apiece. It was crystal clear to everyone at the event that these little girls were growing up fast.

President Obama grew emotional while discussing his daughters at the event. "When I first elected to this office, Malia was just 10 and Sasha was 7," he said. "And they grow up too fast. Now Malia is going off to college...and I'm starting to choke up." We don't blame you, Mr. President.

Traveling The World And Adopting Local Customs

Traveling the world and adopting local customs 16
Traveling the world and adopting local customs
In July 2017, the Obamas took a trip to Barack's childhood stomping grounds in Indonesia, but this trip was a little bit different than the former president watching his mother do anthropological work in the ancient city of Yogyakarta. The family was invited by Indonesian president Joko "Jokowi" Widodo to visit the presidential Bogor Palace in West Java. What they ended up with was an exciting 10-day vacation where they went white water rafting on the Ayung River, visited Yogyakarta, and hit up some of the local temples.

During their visit to Bali's Tirta Empul temple, which is dedicated to the Hindu god of water, Sasha and Malia rocked laid-back athleisure looks. According to People, both of the girls wore baseball caps while their father opted for a casual but put-together short-sleeved polo. The Obama sisters, along with mama Michelle, accessorized with matching yellow sarongs. According to The Huffington Post, sarongs are given to tourists so they can cover up before entering a temple.

Beachside Getaways With Friends

Beachside getaways with friends 17
Beachside getaways with friends
Malia found herself back in the headlines in 2019 — Well, the tabloid headlines, that is. According to the Daily Mail, the former First Daughter was spotted drinking an $80 bottle of Whisper Angel rose at a hotel pool in Miami. The only problem was Malia was underage — the scandal! It's unclear how the Harvard student (or her friends) obtained the vino, but the unnamed "exclusive five-star hotel" staff apparently didn't intervene. However, somehow the paparazzi got wind of the private party and was able to snap some candid shots. Malia looked ultra-chic in a black one-piece, wearing her braided hair half tied up in a pink scrunchie. Yes, scrunchies are totally back.

Sasha also enjoyed spending some time in the Miami sun. In 2017, she was spotted with Joe Biden's granddaughter Maisy in South Beach. The pair were staying at the luxurious Setai hotel, and Sasha rocked a sleek black bikini top with printed shorts. She also wore a hat from Drake's OVO clothing line, which eventually landed her an Instagram shout-out from the rapper.

Malia Obama Catches London's Eye

Malia Obama catches London's eye 18
Malia Obama catches London's eye
In July 2018, Malia hopped over the pond to visit her British boyfriend Rory Farquharson. According to The Telegraph, the pair met at Harvard and were first spotted kissing during a Harvard vs. Yale football game. Oh young love!

During Malia's London visit, the former first daughter looked absolutely smitten with the former Rugby School head boy. The pair packed on the PDA in an underground station and took a romantic walk over Tower Bridge, where they were spotted arm-in-arm. According to the Daily Mail, they also likely went to Bridge Theatre to see Alan Bennett's Allelujah!

Malia was rocking a London-chic look with sensible, $160 Doc Martin boots and pink, wide-legged pants cropped below the knee. She topped the outfit with a white crop top and a light wash denim jacket for the notoriously crispy English breeze. Her accessories were a yellow scrunchie around her wrist (girl loves a good scrunchie) and a Mansur Gavriel mini bucket back in the shade "rococo."

They Didn't Give A 'cluck' At The Turkey Pardoning

They didn't give a 'cluck' at the turkey pardoning 19
They didn't give a 'cluck' at the turkey pardoning
The annual presidential turkey pardon can admittedly be a corny ceremony. Throw in a few dad jokes, and you have a cringe-worthy time for any teenager, but both Sasha and Malia were harshly criticized for seeming too disinterested at the event in 2014. According to the Independent Journal Review, GOP staffer Elizabeth Lauten called out both teens, telling them to "Dress like you deserve respect, not a spot at the bar" and "certainly don't make faces during televised, public events." Lauten later apologized.

Keep in mind, Malia and Sasha endured holiday jokes from the commander in cheese for years: "I want to take a moment to recognize the brave turkeys who weren't so lucky, who didn't get to ride the gravy train to freedom," he quipped in 2016. Can anyone really blame them for rolling their eyes?

At what would have been their last turkey pardon in 2016, the first daughters were given a reprieve of their own and chose not to attend the ceremony. Barack's much younger nephews came out to see the turkey instead, according to the Daily Mail.

Malia Partied Hard At University

Malia partied Hard At University 20
Malia partied Hard At University

While on a college tour in 2015, Malia decided to partake in (or at least observe) some traditional collegiate activities at Brown University. The Daily Caller (via Us Weekly) published a Snapchat screenshot of the first daughter standing close to a table littered with red plastic cups. Twitter exploded with observations from Brown students. "Standing next to Malia Obama at a party nbd," read one of the many tweets (via Buzzfeed); another twitter user claimed the first daughter was "taking shots and playing beer pong." Brown students later apologized for the leaked photos through an editorial in the student newspaper, The Brown Daily Herald, admitting the campus "had no chill" during the visit. Needless to say, Malia chose to attend Harvard University instead.

The aforementioned college visit wasn't the only time Malia was photographed near a beer pong game. In the summer of 2016, the Daily Mail obtained a photo of the first daughter, via Snapchat, standing next to another table of cups and cans. She was allegedly at a house party in Maryland, and though an underage Malia wasn't actually seen holding or sipping a drink, the social media post went viral in a hurry.

Malia Partied In Martha's Vineyard

Malia partied in Martha's Vineyard 21
Malia partied in Martha's Vineyard
Are you sensing a theme? The highly gossiped about Maryland party came just days after police in Martha's Vineyard, Mass.—where the Obamas were vacationing—reportedly broke up a wild party Malia had allegedly attended. Citing "national security," police declined to confirm her presence at the bash, according to the Boston Herald.

Sasha Fangirled Over Ryan Reynolds

Sasha fangirled over Ryan Reynolds 22
Sasha fangirled over Ryan Reynolds
In a moment relatable to sisters everywhere (if sisters everywhere met celebs on the regular), Malia played wing-woman for Sasha when her little sis met actor Ryan Reynolds. The girls were dressed to the nines in ballgowns and attending their first state dinner in 2016, when White House photographer Pete Souza snapped an endearing image of the siblings meeting the Deadpool (2016) star. In the photo, Sasha looks giddy chatting with Reynolds while Malia photobombs her in the background with a thumbs-up. Social media lost its mind.

Leaked Instagram Photo Leaked

Leaked Instagram photo leaked 23
Leaked Instagram photo leaked
Early in 2015, a grainy image emerged of a teenage girl fixing her long, dark hair and staring, lips parted, into the camera. The girl was (gasp!) Malia, in what the New York Post called "one of her first social media leaks since her father took office six years ago." In this day and age, that's an admirable feat for a teenager.

The Instagram pic was posted to Brooklyn rap collective Pro Era's account. In the photo, Malia is sporting a white t-shirt with the band's logo. Coincidentally, the group is led by rapper Joey Bada$$, who was arrested and charged with assault while on tour in New Zealand, reported Page Six. According to The Washington Post, a rep for Bada$$ said the photo was legit and had been received from a mutual friend of one of the group's members.

Until this image, we knew little about this first daughter's musical tastes, though who could forget when the Jonas Brothers surprised Malia and Sasha as part of a scavenger hunt to get to know their way around the White House in 2009.

Malia Allegedly Smoked, Twerked At Lollapalooza

Malia allegedly smoked, twerked at Lollapalooza 24
Malia allegedly smoked, twerked at Lollapalooza
Fresh off her high school graduation, Malia headed to Chicago to attend Lollapalooza in the summer of 2016. After the festival, Radar Online released a video, allegedly showing Malia smoking a cigarette that may or may not have contained marijuana. There were also photos and videos of her twerking at the concert.

Republican Sen. John McCain's daughter, Meghan McCain, even reached across party lines to stick up for the first kid's party antics, tweeting to the tabloid Page Six to "leave Malia Obama alone!" Days after the incident, Malia was spotted wearing a "Smoking Kills" t-shirt—perhaps a tongue-in-cheek reference to the brouhaha?

Worth noting: Barack Obama admitted in his memoir that he smoked pot and "maybe a little blow" as a younger man. Also, marijuana was decriminalized in Illinois, where Malia was allegedly caught with the alleged joint, allegedly.
Malia enjoyed Lollapalooza in July 2017 very much. The former first daughter was spotted dancing to The Killers, writhing around on the ground, and generally having more fun than the rest of us. Sources told TMZ that she spent most of her time backstage with a pal, but that she came out to dance in the general area with plebeians a few times.

...and its aftermath

Dating Is Going To Be Interesting

Dating is going to be interesting 25
Dating is going to be interesting
In November 2016, President Obama admitted his daughters had been dating, and he was okay with it for two reasons. "One is [their mom] Michelle ... she's such a great example of how she carries herself, her self-esteem, not depending on boys to validate how you look or you know, not letting yourself be judged by anything other than your character and intelligence," he told radio station WDCG (via Today). The other reason was much more embarrassing for the Obama girls: the Secret Service.

"There's only so much these guys can do," Obama quipped, referring to his daughters' suitors. "These poor young men come by my house and..." But even the daunting prospect of dealing with the sisters' security detail hasn't thwarted their young gentleman callers, as both Malia and Sasha have already had some high-profile hookups.

Malia was famously snapped smooching her boyfriend, Rory Farquharson, at a Harvard football game. They were also caught canoodling on the streets of New York City. Sasha had her own public fling when photos of her kissing a dude named Matt Metzler at Lollapalooza made the social media rounds in 2016.

Though these ladies still seem to have the eyes of the world on their every move and makeout sesh, here's hoping they're able to carve out some privacy in the future.

They Had Summer Jobs

They Had Summer Jobs 26
They Had Summer Jobs
Even the president's progeny have to earn their own spending money. Sasha spent the summer of 2016 working at Nancy's seafood restaurant in Martha's Vineyard, Mass. — one of the Obama family's favorite spots. She allegedly spent her four-hour shifts doing typical starter-job duties, such as bussing tables, doing prep work, and manning the takeout window, according to the New York Daily News. (The only difference was the Secret Service presence.) Perhaps in an effort to deflect attention, Sasha reportedly went by her full name of Natasha while on the job.

Malia's work experience is significantly more glamorous. She spent the summer of 2015 interning on the set of the HBO series Girls. She got even more Hollywood cred in the next few years when she "spent time" on the set of the Halle Berry series, Extant, and interned for the Weinstein Company in February 2017, according to The Hollywood Reporter. Definitely beats frying up clams, huh?

But Sasha may have gotten the last laugh. After the family moved out of the White house and Malia went off to school, Sasha got a nice upgrade on her living quarters. "She has like this two-room suite — it's all decked out," Michelle Obama told Ellen Degeneres. And Malia's room? "She's got a room up in the attic somewhere," Michelle joked.

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