The Swearing-In Ceremony on Inauguration Day
It’s inauguration day, January 20, 2009, and Barack Obama has just been sworn in as the 44th President of the United States.
Decked out in knee-high socks and school-girl dresses with matching black patent leather Mary Janes, Malia and Sasha attend the festivities. Malia was 10, and Sasha was seven when their father took the oath.
The 2008 Campaign Trail
Campaigning can be tiresome; just look at that yawn! While Sasha looks like she’s paying close attention, Malia would rather be elsewhere. On the campaign trail, making stops in an R.V., it’s casual Friday every day!
The girls are wearing matching flats and cropped denim jeans. Just another example of the sister bond made apparent by coordinating outfits.
The Final Days of the Campaign
Just days before the 2008 election, candidate Obama is exhausted. But here at a rally at J.F.K. Stadium in Springfield, Missouri, we see a beaming father sharing the stage with daughters Malia and Sasha. The grueling campaign kept his family away much of the time, one of his campaign frustrations.
The girls are dressed in regular kid clothes with coordinating blue and red hoodies. It’s a stark contrast to the formality of the Kennedys. Similarly, however, both presidencies made concerted efforts to protect their children from media exposure.
On election night 2008, when the polls closed and the winner was announced, the Obama family took center stage. Fully color-coordinated in red and black, Sasha wore a Gerson & Gerson formal dress, which was later renamed the “Sasha.”
And Malia wore a Biscotti Inc. dress. The modestly priced ensembles quickly made the rounds on fashion runway circuits.
The family chose a colorful mélange on that cold January day. Michelle stunned in a moss green Isabel Toledo print with J. Crew gloves, and Sasha donned an orange and pink coat from the same company.
Malia’s colorful cobalt coat and Barack’s red scarf complete the winter color arrangement. At age seven, Sasha became the youngest person to live in the White House since J.F.K.’s tenure.
The 2009 Easter Egg Roll
At the traditional White House Easter Egg Roll, the girls rock the casual kids look. Malia shows us she knows a thing or two about layering, and Sasha reminds us she likes bright colors.
Her turquoise headband coordinates with Malia’s shirt, but look at that purple skirt! Sasha knows how to make dressing fun.
First Family Vacation to Martha’s Vineyard
Heading to Martha’s Vineyard in 2009, the Obamas disembark Air Force One in their summer best. Mom and girls land the summer look with dark sunglasses, and the girls complete it in seasonal bright whites.
Before the trip, White House Press Secretary Robert Gibbs pleaded with the media to leave the First Family alone. “It is our strong hope and desire that you all, during this family vacation, will respect the privacy of Sasha and Malia.”
The First Family Photo
Snapped by Annie Leibovitz, the most famous celeb photographer in America, the first official portrait of the first family captures the Obamas seated in the Green Room.
It was taken the first day of September 2009; the girls are eight and 11. The First dog Bo is visibly absent. But the First Family looks so splendid in their modern attire; you hardly miss him.
Okay, We Still Miss Bo
This is Bo’s official First Dog portrait. He sat for it following the official portraits of the President and the First Lady. Bo is a Portuguese water hound. The girls named him after Bo Didley as well as other familial appellations.
The non-allergenic breed was chosen to accommodate Malia, but originally the girls wanted to adopt a shelter dog. In the end, Senator Ted Kennedy gifted the 6-month-old puppy to the First Family in April of 2009.
Summer Vacation 2010
The girls, in their summer best, leave behind a Mount Desert Island, Maine vacation as Marine One returns the family to the South Lawn of the White House.
Malia integrates the color scheme with a pink cardigan to match her little sister Sasha’s accent color and a black and white dress similar to Michelle’s. Her baby blue bag ties together mom and dad.
August Beach Day
Sasha picked up a double scoop of Oreo and cake batter ice cream before departing Florida’s gulf coast via Marine One with her family. This 2010 seaside excursion to Panama City Beach included an effort to promote tourism.
The sweet treat came from a local creamery called Bruster’s Real Ice Cream. We don’t know where the colorful summer dress came from, but it was the perfect dress for a perfect day.
On this September Sunday in 2010, the Obamas were discovered walking to nearby St. John’s Episcopal Church in Washington, D.C. The rare sighting found Sasha’s style notably subdued, trading the bright colors she generally picks for subdued purples and blues.
Malia, on the other hand, upped her style game with a snazzy minidress ensemble. Check out those chunky black bracelets. Way to accessorize!
The Annual Turkey Pardon
Here, in 2011, Sasha is taking part in the grand White House tradition of turkey pardoning. Wearing a bright blue blazer and an equestrian print top, she is saying hello to “Liberty,” the aptly named bird.
With the pardon, the president announced that the turkey will “retire to a life of leisure” at George Washington’s historic Mount Vernon. Adding, “Otherwise they’d wind up next to the mashed potatoes and the stuffing.”
Christmas in Washington
At the annual “Christmas in Washington” concert, hosted by Conan O’Brien in 2011, the First Family donned formal attire. Fashion magazines and media outlets alike greeted the girls’ stylish choices with enthusiasm.
They were impressed with Malia’s bold mustard green top and Sasha’s pretty lilac formal dress, veering sharply from mom and dad’s traditional holiday colors. It was becoming clear Michelle Obama was not the only fashion plate in the family.
Nickelodeon’s 25th Annual Kids’ Choice Awards
The Obama girls and Michelle had a fabulous time at the 2012 Kids’ Choice Awards. Meeting boy band One Direction was certainly a highlight. Michelle invited them to the White House following the awards program.
The girls, as we would expect, rocked hot looks, both attired in British brand ASOS. And mom, in a glimmering houndstooth Wes Gordon top, looked like the swankiest FLOTUS ever.
Easter Egg Roll 2012
Out on the South Lawn for the annual Easter Egg Roll, Sasha and Malia accompany their mother.
The assortment of solid colors from Malia’s orange and blue to Michelle’s tri-color solid look is like a basketful of vibrantly painted Easter eggs. Sasha is colorful as usual, repurposing her blue blazer and opting for a rainbow palette. Happy spring!
The 2012 Democratic National Convention
At the 2012 DNC event, the world was reminded that Malia, now 14, and Sasha, 11, were growing up. They came dressed in a sophisticated tailored look, cheering on their father.
Malia wore a royal blue French label, and Sasha looked smart in a checkered frock. The young ladies joined the President on stage to close the 3-day convention.
A Walk Through the Park
This photo depicts Sasha and Malia walking through Lafayette Park hand-in-hand with their father. The trio is heading to church at St. Johns on a crisp October day in 2012.
The girls who frequently make bold pairing choices are particularly outfitted on this day. With prints and patterns and different colors, they somehow make their ensembles coordinate.
Election Night 2012
Elected to a second term, the Obama family celebrates election night 2012. The girls appear sophisticated but add a touch of audaciousness.
Malia accessorizes a conservative look with a hot pink belt, and Sasha accessorizes with a necklace statement. Sasha’s green Chris Benz skirt was sweetly discovered to be a hand-me-down from big sis Malia. The election night party took place on November 7.
The 2013 Inauguration Day Ceremony
Pictured together in coordinating colorful woolen trench coats and matching scarfs on Inauguration Day 2013 is one of our favorite images of the First Daughters.
The image is frequently seen in the media. Sasha is wearing a lavender Kate Spade coat, and Malia is wearing a magenta J. Crew.
The 2014 Visit to China
Now 15 and 12, Malia and Sasha made a fashion impression accompanying the First Lady to China. On the first day of spring in 2014, the girls joined their mom for a seven-day trip. Here they are with Chinese President Xi Jinping and his wife, plus, grandmother Marian Robinson.
The girls, stunning as usual, are in flats; yet still towering over the Chinese dignitaries. Sasha is in a white-belted red dress with black patterned tights, and Malia wore a big floral print matching skirt and crop top from Topshop.
Family Portrait Easter Sunday 2015
The First Family attended Easter services at the Alfred Street Baptist Church in Alexandria, Virginia. They shared their spring 2015 family portrait with Instagram followers captioning, “From the Obama family to yours, Happy Easter!”
Sasha brought out her narrow, white belt, pulling together an orange sleeveless top and a short yellow flare skirt, while Malia opted for a patterned dress in purples and blues. Bo is joined by Sunny, who rounded out the family in 2013.
The 2015 Visit to 10 Downing Street
The Obama girls joined the First Lady to visit Prime Minister David Cameron and to have tea with Prince Harry. It was a lovely day as Prince Harry gets on splendidly with the First Lady.
Malia and Sasha, princesses for the day, dressed in Kate Spade. Their dresses were similarly styled, each donning a sleeveless above-the-knee dress, Malia in red and Sasha in teal.
The European trip included a stop in Venice. Touring the U.S. Pavilion of the Venice Biennale, Sasha wore a multi-patterned dress with a black skater skirt.
Malia wore a navy skater skirt and stayed casual with a denim jacket.
Martha’s Vineyard 2017
Post-vacation blues? Malia and Sasha return from an extended family vacation in denim-blue sundresses. Particularly adorable is Sasha’s chambray frock with white embroidery by Tory Burch.
Martha’s Vineyard is a favorite of the Obamas, and they stay in Chilmark, a quaint region of the beautiful island off the coast of Massachusetts. They celebrated Barack Obama’s 56th birthday on that leisurely, post-presidency vacation.
Hosting the Pope
In 2015, the First Family was graced by a September visit with Pope Francis. Greeting the pontiff on the tarmac at Joint Base Andrews airport, the First Lady and the First Daughters wore feminine ensembles with slightly longer skirts, just beyond the knee.
Both girls wore black tops. Sasha paired hers with a pink, grey, white and black Kate Spade asymmetrical color block skirt. Malia chose to wear a white and black floral skirt at the historic event.
The 2015 Turkey Pardoning Ceremony
Malia and Sasha, fashionable as always, donned American Apparel, Alice + Olivia, and Topshop for the annual turkey event.
As the president gave the oath to spare the life of Honest, the bird gobble-gobbled, and the First Daughters giggled. It was nice to see them matching once more. Black tights and slouchy socks set off their casual but trendy looks.
The 2016 State Dinner
Hosting Prime Minister Justin Trudeau, the White House state dinner honored our Canadian neighbor. The girls dressed in formal attire for the posh event.
Malia looked all grown up and glamorous in a beaded strapless gown, and Sasha’s sleeveless embroidered sheer bodice in deep reds and black looked very mature as well. The First Daughters did not make an entrance on the red carpet, choosing a typically low-key appearance.
Visiting Havana 2016
This time Malia dressed brightly in an Alice + Olivia tangerine-orange cotton frock.
The spring visit to Cuba offered Malia an opportunity to serve as translator-in-chief for the president. Sasha dressed in a Tory Burch skirt ensemble, stripes on top, and patterned flare skirt.
Back to Martha’s Vineyard
It’s summer vacation, 2016, and the First Family is heading off to their favorite destination. The girls are in bright white seasonal attire, Malia wearing a strapless Reformation sundress and Sasha mixing it up with a black-and-white striped blouse and a layered necklace look.
The media was permitted to photograph the youngest Obamas only during official visits and scheduled family outings, as opposed to going to school, for instance. So it just seems like they were always on vacation.
Returning from Summer Vacation
It’s not as much fun coming back from vacation, but Sasha dressed adorably.
Wearing a bohemian style short dress with coordinating wedge tie-up sandals, she looks like a fashion plate.
Malia Makes a Statement at the 2016 Made in America Festival
Summer 2016 finds Malia, in a Harvard cap, at the Made in America festival. Her handmade t-shirt with a statement invites attention. President Obama claims he quit smoking in 2007 because he feared his wife.
She says, however, he did it for the girls. “I think that he didn’t want to look his girls in the eye and tell them that they shouldn’t do something that he was still doing,” Frist Lady Obama said in a 2012 interview.
Lighting the 2016 Christmas Tree
Little sister Sasha soaked up the attention as the only child at the 2016 Christmas tree lighting ceremony. Meanwhile, Malia was off spending her gap year in N.Y.C. exercising newly acquired adulting privileges.
Sasha dressed cozily in a dark blue velvet coat from the brand Opening Ceremony. She wore it for the Obamas final tree lighting ceremony as First Family. The event included a range of pop star performances. Chance the Rapper caught Sasha’s attention as she was caught lip-syncing along to her favorite part.
President Obama’s Farewell Address
In January of 2017, the president said his formal farewells to the office.
This time, Malia took the spotlight while Sasha stayed back to study for an exam. She looked stunning in a white and black Cinq à Sept dress.
Hanging Out in Soho
Malia is now 18 years old and a former First Daughter. She moved to NYC to live on her own. Here, she is pictured hanging out in the Soho district in February 2017.
Her beautiful magenta parka with faux-lined hood hides a plaid flannel shirt and black turtleneck.
Hanging Out in the City
Living in New York and working as an intern, Malia enjoys a casual lunch with a friend.
Spotted in May of 2017, she’s in skinny jeans and a NY Giants baseball cap. It’s just a few short months before her gap year ends and her first semester at Harvard begins.
The Former First Family Visits Indonesia
In the summer of 2017, President Obama was out of office but took a 10-day diplomatic trip to Indonesia.
The girls got to go too and are pictured here at a temple in Bali wearing golden yellow sarongs and casual attire. The sarongs are customary and worn to show respect.
Malia Goes on a Date
At Harvard, Malia met Rory Farquharson, a son of a successful British investment manager.
The two met hanging out at a Harvard-Yale football game, and here they are on a date in New York. Malia is wearing a black parka and a floral print dress with a pair of Doc Martens, adding a touch of punk.
Malia’s Boyfriend Meets the Family
Spotted together on a date in London, Malia wears a flattering white sundress paired with edgy Docs for some serious walking. Their relationship notched up a level when her father took Rory in to stay with the family because of a visa issue.
Obama explained on the Bill Simmons podcast exactly what happened. “He’s British … wonderful young man, and he was sort of stuck because there was a whole visa thing, and he had a job set up. So, we took him in, and I didn’t want to like him, but he’s a good kid.”
‘From Our Family to Yours, Happy Thanksgiving!’
This post-presidency holiday portrait pictures Malia, now 21, in a dainty lilac shirt dress and 18-year-old Sasha in a silky spaghetti-strap black gown.
Michelle Obama posted the family photo to Instagram on Thanksgiving 2019.
Malia and Sasha Give Rare Interview
Michelle Obama released her memoir “Becoming” in 2020, and a documentary of the same name was released shortly after. In a rare appearance, the Obama daughters were interviewed as college students.
Sasha expressed pride in her mother’s accomplishments, and Malia observed, “those eight years weren’t for nothing,” adding, “people really believe in love and in hope and hope in other people.” In casual dress, Sasha’s ripped jeans and graphic tee make a statement while Malia is in soft pastels.
Sasha Rocks a TikTok Moment
Michelle Obama made every effort to keep the girls free of social media as a First Family, mostly because of their high-profile status. But every kid is going to TikTok, Tweet, and Insta message eventually.
Sasha, as usual, has the layered jewelry look dialed. She’s wearing a casual hoodie at a college party. The sophomore is performing a new dance craze and singing along to a pop song with her friends.
On the Beach in Honolulu
Candidate Barack Obama took his family back to his home in Hawaii the summer before his election.
Spending some quality time before the White House commitment sets in, the young girls were photographed with their father enjoying the seaside. The girls are pictured in beach casual play clothes.
An Inspiring Image
Malia doesn’t mind posting paparazzi pictures of herself to her Instagram page.
Here she is in a cute black-and-white frock, sans jewelry as she seems to prefer. She shared the photo accompanied by an inspirational message on September 6, 2019.
White House Introductions
In 2008, the Obama girls visited the White House for the first time. Bush twins Barbara and Jenna Bush were on hand to welcome the new First Sisters and give them a tour. Here Jenna is introducing Malia and Sasha to White House staff members.
The Obama girls are dressed in cute girl’s department store outfits, much more coordinated than their later outfits displaying true styles and vibrant colors.