Malia and Sasha Obama were little girls when their dad was elected to be the 44th president of the United States. Barack Obama was first a state senator in Illinois, then was elected to be a U.S. senator representing the state of Illinois, and then became the Democratic party nominee for president in 2008. Their mother Michelle has, among other things, been considered an influential fashion icon for many years.
The girls, for much of their father’s time in office, were young and their fashion and style expertise really wasn’t much of a consideration. They’ve grown up, however, and especially since leaving the White House in January 2017, they’ve shown off their flawless fashion and will surely continue to flaunt their individual senses of style — no longer in the immediate public eye — for many years to come.
Returning from vacation in Hawaii
While they weren’t technically out of the White House yet, the Obama family went to Hawaii over the winter holidays during their final vacation in the White House and returned to Washington D.C. after the New Year. While some choose to travel in their athleisure finest, Sasha and Malia still managed to be somewhat fashionable, even while traveling such a long distance.
Malia stepped off the plane in an all-black, comfortable outfit with great shoes and a maroon coat, her hair pulled back into a slightly-messy ponytail, elevated with a twist on the side of her head. Sasha wore a fleece-lined denim jacket over her outfit with trendy, black-framed glasses. Sasha pulled her hair only partially back, but, like her older sister, had a twist on the side of her head. Fashionable after a long flight, that’s the dream.
Malia leaving for Chicago
You already know that Sasha and Malia look flawless when traveling, but Malia’s outfit while traveling to Chicago to attend her father’s last major speech as president was definitely a standout. She wore her elegant black and white dress, black ankle boots and sheer black tights that she’d be wearing to the speech later that night, but she topped it off with a gorgeous camel-colored coat, a rich brown leather travel bag, and a structured black handbag.
According to Teen Vogue, her camel coat is from 3.1 Phillip Lim. Channel Malia’s keen sense of style this fall and winter by pairing camel and black for a timeless look.
Malia at the Chicago farewell address
Former President Barack Obama gave his final speech to the nation on January 10, 2017 from McCormick Place in Chicago. While his wife Michelle and daughter Malia (as well as Vice President Joe Biden and his wife Jill) traveled to Chicago for the speech, Sasha stayed behind in Washington because she had a test the next day at school, according to Us Weekly.
Malia’s flattering and interesting, yet understated black and white dress was by Cinq a Sept and she paired it with sheer black tights, black ankle boots, and a black choker necklace. She wore her hair simply, as well. Classic, but still with a little bit of personality.
At Joe Biden’s Medal of Freedom ceremony
Then-President Barack Obama honored then-Vice President Joe Biden with the Presidential Medal of Freedom on January 12, 2017 in the White House State Dining Room and both Malia and Sasha attended the ceremony. Malia looked elegant in navy, while Sasha showed off her great taste in a complementary navy, white, and gold patterned dress. These sisters certainly don’t always dress alike, but when they wear complementary outfits, they both definitely make the best dressed list.
Malia going to her internship
According to Vanity Fair, after the Obama family returned from their post-presidency vacation, Malia moved to New York City to take an internship with legendary film producer Harvey Weinstein. Over the course of her internship, Malia was frequently photographed around the city.
On this particular day, according to AOL, Malia donned an army green crop top, high-waisted denim, a leather backpack, and white sneakers. She pulled her hair back into a carefree look, which looked both pulled together and very casual.
Malia out and about in New York City
In March 2017, while Malia was interning at The Weinstein Company, she stepped out in a decidedly ’90s, slightly retro look. According to BET, the former First Daughter wore stylish, throwback K-Swiss sneakers with her color block windbreaker jacket and light-washed, boyfriend fit jeans. Her confidence in the look will convince even the fiercest critic. If this look doesn’t say casual, fashionable spring weekend fun in the city, I’m not quite sure what does.
Malia eating at a restaurant
During Malia’s time in New York City, she was often photographed out around town. According to InStyle, Malia spent time out with a friend in New York City in May wearing a New York Giants cap, darkish denim jacket, cropped, dark-wash jeans, black booties, and a white shirt. Malia just might be better at the casual weekend look than anyone else. She also demonstrated that it really can be stylish to wear jeans with a denim jacket, in case you still weren’t sure about that.
Sasha at her sweet 16 party
Though Sasha Obama was just a little girl when her dad was elected president, she grew up over the eight years the family spent in the White House. Sasha turned 16 in 2017 and celebrated in style with her friends and family.
According to the YBF, the party took place in May, though photos of the event didn’t become public until June. Harper’s Bazaar reported that Sasha’s red satin slip dress was a Jill Jill Stuart dress, which she paired with delicate gold necklaces. Talk about style.
On vacation in Bali
In June 2017, the Obama family traveled to Indonesia. The trip wasn’t necessarily full of fashionable moments (the best vacations usually aren’t), but while visiting the Tirta Empul Temple, Sasha, Malia, and Michelle wore yellow sarongs over their clothing, which is the custom when visiting holy sites, according to InStyle.
Sasha wore a simple black spaghetti-strapped blouse, a baseball cap, and sunglasses, while Malia previewed her Harvard move-in outfit in the same Alexander Wang t-shirt she’d later wear there, leggings, and a baseball cap.
Malia at Lollapalooza
Both Malia and Sasha went “home” to Chicago for Lollapalooza, the annual music festival held each year in the city’s Grant Park. There are tons of great fashion moments each year at Lollapalooza, but the stylish former first daughters are often a highlight.
At the 2017 festival, after they’d left the White House, Malia attended several shows including Aminé’s, according to Vibe. Malia wore a gray-blue tube top with dark-washed denim, which is perfect for a music festival or the perfect summer dinner on one of Chicago’s many patios.
Malia moving in at Harvard University
College move-in can be an exciting, stressful, and a little bit sad experience all at once. Malia Obama moved in at Harvard in August of 2017, after taking a gap year the year prior, interning at The Weinstein Company, working on the set of Girls, and working as a production assistant on the set of Extant, according to The Boston Globe. Malia wore a t-shirt underneath a simple, casual black dress to move in to her freshman dorm (assisted by her parents, of course), keeping things stylish, yet comfortable.
Malia and Sasha’s fashion has evolved a lot over the years
Now that Malia and Sasha have grown up and left the White House, they have more control over their fashion and sense of style than ever before. They’re no longer in the public eye as frequently as they used to be and they’re no longer members of the first family.
“Everyone is keeping an eye out for what they’re doing and who they’re wearing,” Hilary Novelle Hahn, founder of The Style Club, told me. “I think they’re always going to be on everybody’s radar, especially now that they’re getting older and their styles are evolving and maturing along with them.” Each of the young women has come into her own, taking after their stylish mother and becoming budding fashion icons in their own right.