Since leaving her White House days behind, Sasha Obama has not shied from wearing daring outfits. Perhaps her most boundary-pushing outfit came at a Halloween party held by Billie Eilish in October 2024. Unsurprisingly, multiple celebrities attended the shindig hosted by the “Hit Me Hard and Soft” artist, including Kaia Gerber, The Kid Laroi, Kiernan Shipka, and Eilish’s brother, Finneas. Sasha did not attend the event solo, as her sister Malia Obama also dropped by in a white tank top, short denim skirt, knee-high boots, black top hat, and faux snake around her neck. She appeared to be channeling Guns N’ Roses guitarist Slash for her Halloween look. Malia’s costume may have been spicy, but it was Sasha’s outfit that drew the most attention.

The University of Southern California alum wore multiple layers: a baby blue cropped tee that left her midsection exposed, a rust-colored vest, and a stylish black leather trench coat. Sasha left the coat undone to showcase her outfit, which also included tiny striped shorts with oversized pockets. The former first daughter completed her ensemble with a black leather belt slung low around her waist and a pair of brown slouchy boots. The shorts and boots combo highlighted her legs.

Photos of the daring outfit re-circulated in February as part of a viral post on X, formerly Twitter. “[S]he’s always looking good as f*** i love her,” one fan wrote in response to the tweet. “She’s so weirdly fly I love it,” another added. Meanwhile, not everyone was a fan of her outfit choice. “She look homeless,” an X user replied. Despite the virality of the look, this was not even the most inappropriate outfit Sasha was caught wearing.

Both Sasha Obama and Malia Obama pulled off bold looks when they attended an afterparty held by Drake at The Bird Streets Club in Los Angeles in August 2023. Malia was photographed leaving the party with her sister in a risque outfit: a pair of body-hugging floral-print pants and a long-sleeved lace-up top that left plenty of skin exposed. Sasha upstaged her sister with an even spicier ensemble. The younger Obama daughter sported a tiny black bralette top and a pair of loose-fitting cargo-style pants that hung well below her waistline. Her hair was braided and tied back in a ponytail, and she accessorized with a pair of black flip-flops and a large purple purse. The revealing looks were bashed online by people who were surprised to see the Obama girls dressed so scandalously. “Where did these young women get their clothes? Especially Malia….she looks like she is going to lose her pants,” one person on X wrote. “All that money and that’s the best they can do????” another commented.

Showing ample skin at the Drake after-party was not a one-off for Sasha. A year earlier, she was photographed on the University of Southern California campus in a two-tone layered crop top that was brown with white underneath. The college student also had on a pair of baggy-fit blue jeans that hung off her waist, which left her white underwear exposed. Along with matching her top, the exposed undergarment also complemented the white JW Anderson woven bag she carried. Sasha’s long hair was tied in a ponytail, which was flung over her shoulder, and she completed the look with a slew of necklaces and rings.