Sasha Obama’s Most Daring Outfits to Date

In April 2009, the Obama family welcomed Bo, their Portuguese water dog. What Sasha Obama chose to wear, however, likely wasn’t the most optimal for running around and playing with a puppy. Instead, she wore a dark-blue four-button knit top, brown capri shorts, black ballet flats with hot-pink ankle socks, and a teal headband. By the looks of it, the weather was rather dreary. We just hope she didn’t slip and fall while playing fetch with their new companion. While we do miss the days when we let our imaginations run wild to put together an outfit, this look was less than practical for the outdoors activity.

Sasha Obama’s incredibly chic street style may be a sight for sore eyes now, but it sure took her a while to build up her wardrobe. On Thanksgiving 2011, she decided not to opt for a dress or skirt, but instead some navy skinny jeans, a horse-covered graphic tee, and a sky-blue blazer with black trimming. Certainly some interesting pieces in the mix for a milestone calendar event, but we can’t say we didn’t wear similar atrocities at 10 years old.

For the annual turkey pardon in 2013, Sasha Obama opted for a green panda graphic sweater with a navy overcoat, maroon infinite scarf, red skinny jeans, and combat boots with bright-yellow laces. We don’t know if she couldn’t decide on a color palette, or simply thought it was Christmas. Regardless, the color-mixing didn’t have the most positive outcome for the youngest Obama daughter, especially on a day where all eyes were on her and her family and a slightly more refined style was expected.

Sasha Obama’s Thanksgiving outfits in 2011 and 2013 weren’t the last too-casual turkey-day looks from the former first daughter. In 2014, she opted for a maroon minidress under a white cardigan, matching knee-high socks, and combat boots. One particular critic had some qualms with her and her sister’s outfits, and was later rightfully called out for her harsh comments. Elizabeth Lauten, the communication director for Congressman Stephen Fincher, took to X with a now-deleted post, scolding the teenage girls. “Act like being in the White House matters to you,” she wrote (via The Guardian). “Dress like you deserve respect, not a spot at a bar.”

There’s no written rule that says the president and his family must be color-coordinated at all times, but when one member opts for a different palette, it’s fairly obvious. In June 2013, when leaving for a trip to Africa, Barack, Michelle, and Malia Obama all opted for darker, simple color palettes; Barack and Malia Obama, who has also had a stunning style transformation, coordinated in navy while Michelle stepped out in a black, white, and gray striped dress. Sasha, on the other hand, decided on a vibrant-pink babydoll dress, a colorful tote bag, and teal flats. It’s giving funeral attendees, while Sasha is heading on vacation.

In April 2025, musician Destin Conrad posted a carousel of images to Instagram promoting his new album, and in one pic, he can be seen cozying up to Malia and Sasha Obama. Sasha kept it simple with a white tank top rolled up under her bra and a pair of low-rise jeans, incorporating her boho-chic aesthetic with a statement necklace and braided belt. Some outlets described the ‘fit as “risqué,” leading to accusations of a “wild party” by the Daily Mail. Though many fans support Sasha’s right to wear whatever she wants, this definitely ended up being a more controversial look.