CELEBRITY STYLE

Sasha Obama shows off effortless street-style look with the perfect winter skirt

Sasha is dressed for winter in LA

JANUARY 15, 2026 9:55 PM ESTJAN 15, 2026, 9:55 PM EST

Sasha Obama is proving, yet again, that style doesn’t take a day off, even when the day’s agenda is a quick stop at a tailor. This week, the 24-year-old was spotted in Los Angeles looking effortlessly polished while picking up a fitting, turning a routine errand into a full-on street-style moment.

For her latest outing, Sasha kept it cool and casual, wearing a fitted black long-sleeve top paired with wide-leg navy trousers. A wide brown belt sat low on her hips, and oversized sunglasses, subtle jewelry, and a large blue tote completed the look.

Flip-flops kept it relaxed, balancing comfort and low-key sophistication. Sasha’s off-duty style has been on point all month. Just days earlier, on January 6, she was photographed post-gym in West Hollywood in an all-black athleisure set.

A black tank top and matching leggings formed the base, but it was the styling details that made the look pop, including a light gray headband channeling late-’90s/early-2000s nostalgia, a slouchy oversized tote for laid-back structure, and trendy clogs that kept it practical but fashion-forward. Accessories were key, as Sasha rocked toe jewelry, a nod to early-2000s pop culture.

Sasha’s polished, effortless vibe isn’t just a passing phase; it’s a style consistency she’s maintained since moving to Los Angeles. Last summer, during a night out with her sister, she rocked a Jean Paul Gaultier long-sleeve printed shirt paired with True Religion skinny jeans tucked neatly into knee-high black boots, a move straight out of the Y2K playbook.

Sasha Obama revives Y2K trend with toe jewelry in West L.A. sighting — Sasha leaned fully into Y2K styling, accessorizing with toe jewelry, a trend once synonymous with early-2000s pop culture.

Sasha amped up the look with a chunky belt, oversized bracelets, and colorful jewelry, proving she can take bold, nostalgic pieces and make them feel completely modern and effortless. Meanwhile, Malia complemented her sister with a denim mini-skirt, grey corset top, and dark green jacket.

Last winter, she and Malia were spotted enjoying a casual family dinner with their dad, Barack Obama, in LA, and of course, the fashion game was strong.

Barack Obama enjoys a family dinner in Los Angeles with daughters Malia and Sasha

The sisters’ looks were coordinated without feeling matchy. Malia wore a denim mini-skirt with brown tights and leather boots, topped with an oversized brown leather jacket and a striped shirt, while Sasha paired baggy jeans with a black top and a long brown coat.

Earlier this month, Sasha and Malia were photographed having dinner with their dad Barack Obama — Sasha and Malia were photographed having dinner with their dad Barack Obama

Barack kept it casual in gray trousers and a navy jacket, proving that effortless style can run in the family. The duo may have been doing a little shopping before dinner, but Sasha’s signature mix of comfort and polish was fully on display.

Since relocating, Sasha and Malia have been seen attending exclusive events, running errands together, and enjoying LA’s lifestyle, all while cultivating a wardrobe that balances California ease with subtle nods to her own style.

While Malia continues to make waves in film, Sasha has been spotted embracing relaxing afternoons of knitting, reading, and hitting the gym, showing that her personal style extends beyond clothing into the way she navigates her daily life.