40 Outfits That Show Malia And Sasha’s Transformation From First Daughters To Fashionistas

Back in January 2005 a pre-presidency Barack Obama was sworn into the 109th United States Congress, alongside his wife Michelle and young daughters. And the fact that they got a six- and three-year-old to look that neat and professional tells you all you need to know about the Obamas’ excellent parenting skills. Michelle was even able to co-ordinate her scarf with Malia’s dress.

When Barack Obama started his presidential campaign in 2007, he brought the young Malia and Sasha along with him. They might’ve been a little bored – check out Malia’s big yawn in the picture – but they brought their under-ten fashion game. The sisters even have coordinating outfits and matching jeans here.

Towards the end of Barack Obama’s 2008 campaign, he took Malia and Sasha with him to an event in Missouri’s JFK Stadium. You’ll note that both little girls are dressed in red and blue to match the flag behind them. Did their parents (or they themselves) plan for that? Or was it just a happy coincidence?

The Obamas brought their A-game for fashion on Election Day. When Obama was declared the winner, all eyes were on them. Malia’s $110 Biscotti Inc. outfit quickly became a runaway hit with consumers, and so did Sasha’s $72 Gerson & Gerson gown. In fact, the younger Obama’s dress was later re-titled “Sasha” by the manufacturers.

Barack Obama’s inauguration was an absolute dream for fashion fans. There was Michelle’s stunning Isabel Toledo outfit, first of all, and then there was that incredible hat Aretha Franklin wore. But the young Obamas kept up with the adults. Sasha and Malia wore colorful coats, with Sasha’s coming from J.Crew – the same company that provided Michelle’s green gloves.

In 2009 Malia and Sasha partook in their first Easter egg roll, a White House tradition. There they got to show off their casual ensembles for the first time, too. They wore bright colors, cute pinks for Sasha and more mature blues for Malia. The highlight here was probably the younger Obama’s adorable polka-dot leggings and Converse shoes combo.

When the Obamas went to Martha’s Vineyard in 2009, the two girls looked a bit like miniature versions of their mother. They were all wearing stylish shades of white, plus sunglasses. But that’s not remotely a bad thing, since Michelle is a fashion icon in her own right. This holiday may mark the beginning of the Obama girls’ fascination with big bags – they seem to love them.

In 2009 Annie Leibovitz took a picture of the First Family in the White House. They were all color-coordinated in monochrome outfits and looked perfect. Around the same time, Michelle was being criticized by the press for always choosing sleeveless outfits – perhaps the girls wearing the same here was them subtly sending a message?

The big bags are back! And here you can see Malia and Sasha, having previously worn coordinated outfits pretty frequently, start to unco-ordinate. Both are wearing something appropriate for their age group. Malia, as the oldest daughter, sports something not unlike what Michelle’s got on, while Sasha has a more girly outfit.

Hands up if there’s no way your parents would let you eat ice cream if you had your nice clothes on. Well, that rule isn’t one the president’s daughter has to follow! In 2010 the then nine-year-old Sasha Obama was snapped getting the messy snack while wearing this absolutely stunning dress. And it was all fine, don’t worry.

In September 2010 President Obama and his family went to St John’s Episcopal Church, which is close to the White House. The press were there, too, so they all had to look perfect. And Sasha and Malia pulled this off with aplomb. Both wore stylish dresses – black and white for Malia, cute blue for Sasha – and subtle jewelry.

Sasha attended the traditional White House turkey pardoning in 2011, and chose an animal print shirt to wear. Sadly, it didn’t feature a turkey, but rather another animal often found on farms: a horse. Paired with a bright blue blazer and a cute red heart necklace, it looked fantastic on her.

Everyone loves dressing up for Christmas and the Obama daughters are no exception. In 2011 they went onstage in Washington wearing beautiful dresses that the HuffPost adored. The website even wrote of Malia, “The 13-year-old has been spotting in several fashion forward outfits lately and is quickly becoming one of our favorite style gals to watch.”

Dressing for the Kids’ Choice Awards can’t be easy. It’s a high-profile entertainment event with plenty of photographers but it’s, well, for kids. Sasha and Malia were kids at that point, of course, and they pulled out all the stops. Both wore outfits from the British brand ASOS which were just the right side of casual.

The Obamas seem to use the Easter egg roll as an excuse to bring out their most colorful clothes, and why not? You’ll notice that Sasha has the same blue blazer she wore at the turkey pardoning in this photo. If you find a piece you really like you gotta stick with it, and the Obamas are definitely down to earth enough to recycle.

Malia and Sasha wore super-chic outfits at the 2012 DNC. 11-year-old Sasha had a grey Anthropologie dress with a yellow belt, and Malia sported a blue number from H&M with her nails done in the same color. Even though they were stars of the show, their father told them from the stage, “You still have to go to school tomorrow.”

This photo shows Malia and Sasha on their way to St. John’s with their dad in October 2012. And they’re providing an absolute masterclass on how to dress when the media are watching. Both their outfits are stylish, eye-catching and age-appropriate. Plus, they’re wrapped up warm against the weather as well.

The Obama family did, of course, have not one but two successful election nights. For their appearance onstage in 2012 Sasha and Malia didn’t put a single foot wrong. The media noted that the green Chris Benz skirt Sasha sported had actually once belonged to Malia, which was a sweet little touch.

Obama’s second inauguration was obviously a big event, so Malia and Sasha brought out their best and most stylish coats. The White House reported on which designers they chose while the eyes of the world were on them – Sasha’s purple coat was from Kate Spade, and Malia’s fuchsia one from Obama favorite J.Crew.

In 2014 the Obama daughters went on a diplomatic trip to China with their mother. While 12-year-old Sasha wore a fairly simple red dress to mirror her mom’s, Malia did something different. Us magazine wrote of her, “The true star of the foreign photo op, however, was 15-year-old Malia – who resembled her stylish mom more than ever – in a high-waisted floral skirt and matching crop top from Topshop.”

The Obama family didn’t actually release that many official portraits featuring the girls. This one, taken for Easter celebrations in 2015, was only the third. But it nicely shows how the two young women were evolving their fashion styles. And you’ll note there wasn’t a sleeve in sight. Deploy the “right to bare arms” joke now…

In June 2015 Sasha and Malia went on a trip to England with their mom. For their visit with the prime minister at 10 Downing Street, they both picked stylish Kate Spade dresses – a bright red one for Malia and a turquoise number for Sasha. The First Daughters looked every bit like princesses on that day.

The two Obama girls got to do a lot of travelling in 2015 – they also went to Venice in Italy. While there, this photo was snapped, which perfectly demonstrates their evolving styles. The girls don’t match like they used to anymore. Instead, Sasha is opting for a chic, intricately patterned summer dress while Malia rocks casual denim.

One perk of being a First Daughter is that you get a lot of holidays. Here, the girls are exiting the helicopter that took them to Martha’s Vineyard in the summer of 2017. Malia’s back in denim and Sasha has another patterned dress – plus, don’t forget the oversized bags. And their dad has thoughtfully gotten dressed in the same color, too!

What do you wear to greet the Pope? That’s the sort of question Sasha and Malia had to answer in their day-to-day lives as First Daughters. When His Holiness came to America in the fall of 2015, Malia wore a flowery dress and Sasha a gorgeous pastel skirt from Kate Spade.

The Obama girls always brought it for the annual turkey pardoning. At the 2015 event Sasha looked like a geek-chic queen in her glasses and neat skirt. Malia, on the other hand, went for something a little more edgy with her color-blocked jacket. Both girls had shopped at American Apparel for their outfits, it turned out.

Malia and Sasha maintained a very low profile throughout the 2016 White House Dinner. We do know a little about their dresses, though – they were created by Naeem Khan and were quite a bit more grown-up than the Obama girls’ usual outfits. Malia’s was strapless, and Sasha’s had sheer panels in the front. But because the girls were still so young, photos and comments were kept to a minimum.

Malia proved red was one of her colors when she went to Havana with her family in 2016. She wore a stylish dress from Alice + Olivia, a New York-based brand. But she wasn’t just there to show off her wardrobe – during that trip she also served as a Spanish-language interpreter for her father.

The Obama girls chose white outfits for their summer vacation in 2016. As they boarded Marine One to head for Martha’s Vineyard, photographers got a good look at their stylish ensembles. Malia had on a Reformation sundress, and Sasha chose a stripy shirt with a belt and chic white skirt.

Sasha is really good at dressing for vacations. Returning to Washington, D.C., with her father in 2016, she rocked this boho dress and wedge shoes, using a funky backpack and fashionable chokers for accessories. It was the perfect summer look and proof she was getting more confident with her styles.

Malia shook things up in September 2016 with her festival outfit. She sported a cap from her own college, Harvard, plus cutoff shorts, shades and a t-shirt. It was the latter that drew the most comment, as it read “Smoking Kills” and she might have created it herself. Was she, like so many White House occupants before her, using fashion to send out a message?

Sasha was the sole Obama daughter at the 2016 White House Christmas tree lighting, as Malia was away on her gap year. She got all dressed up for the occasion and wore a dark blue velvet coat from the brand Opening Ceremony, plus skinny jeans and one of the chokers that were fast becoming her trademark.

It was Malia’s turn to go solo at her father’s all-important farewell address in January 2017, because the then 15-year-old Sasha had an important exam the next morning. So Malia was fashionable enough for two that evening. She wore a black and white dress, from the company Cinq à Sept, and matching tights.

Even after Barack Obama had left the White House, the former First Daughters remained people of interest. A photographer snapped this shot of Malia going about her day in Soho wearing a fabulous oversized coat, complete with sneakers, socks and stylish bag. It’s clear that fashion is something that comes naturally to her.

This photo is a great snapshot of what Malia’s post-White House life looks like. She doesn’t have as much pressure on her and can simply enjoy herself with friends in New York City. Here, she’s wearing Chelsea boots, a denim jacket and black jeans. And she also happens to have a New York Giants hat – her father name-checked that team back in 2012.

The Obama girls obviously weren’t First Daughters anymore by 2017, but they still served as diplomats for their country in some respects. In June of that year they accompanied their father on an Indonesia trip that the media took an interest in. Sasha and Malia wore casual clothes, but they also sported the yellow sarongs that tourists are asked to don when going into temples.

Malia Obama has a boyfriend now! Feel old yet? The guy in question is a Brit named Rory Farquharson whom Malia met at Harvard. Here she is out in New York City with him, wearing a stylish black jacket appropriate for the January weather. Along with that she’s got a floral dress and Doc Martens worn with socks.

In November 2019 Michelle Obama posted a picture on Instagram with the caption, “From our family to yours, Happy Thanksgiving!” It was a fascinating glimpse into how Sasha and Malia’s fashion sense had evolved. Malia, 21, had a lilac shirt dress on while 18-year-old Sasha wore a black gown with a high slit.

In 2020 the documentary Becoming, all about Michelle Obama and her achievements, was released. And Sasha and Malia popped up in it for a rare interview. Malia wore a simple shirt-and-jeans combo but Sasha’s Aaliyah graphic tee was very much the standout. Instantly after she was seen in it, it sold out.

The Obama daughters stayed more or less away from social media… until late 2020, when some TikTok videos featuring Sasha suddenly went viral. In them she’s wearing regular casual clothes, but her jewelry game is absolutely on point. And she also appears to be having fun, which is great to see!