Outdated Trends The Obama Sisters Have Been Caught Wearing

It's often said that fashion has no real rules. There is perhaps one: wear whatever makes you feel good. But when you're in the public eye, every choice — intentional or otherwise — becomes part of a larger conversation. Consider the Obama family. In her memoir, "Becoming," Michelle Obama revealed how every outfit she wore as First Lady carried weight, noting: "Optics governed more or less everything in the political world, and I factored this into every outfit." Her approach was strategic, and after enlisting the help of stylist Meredith Koop, she cultivated a style evolution that still resonates today.

Sasha and Malia Obama, on the other hand, have had more freedom to experiment with fashion, but that hasn't meant complete privacy. Growing up at the most famous address in the world, their wardrobe choices — whether they're donning streetwear casuals or they're red-carpet ready — have been more public than most. Like anyone, they've had fashion moments that reflect the trends of their time, some of which may now feel like relics of the past. But a deep dive into the outfits of the Obama sisters offers a time capsule for the ever-changing landscape of style, where trends rise and fall. 

While some of their past sartorial choices may feel outdated now, the former First Daughters have aged with grace. And if history tells us anything, it's that fashion is cyclical: what's out today could be coming back with a vengeance tomorrow.

Some trends are timeless; others are neon. It's loud, attention-seeking, impossible to ignore. It's had its moments: first in the aerobics boom of the '80s, then in the Y2K club scene, and most recently, in its Brat-fueled 2024 resurgence, thanks to Charli XCX. But neon follows a predictable pattern: it burns brightly, draws attention, overstays its welcome, and vanishes until the cycle starts all over again.

Sasha Obama's 2010-era neon ensemble — a punchy orange top paired with a highlighter-green skater skirt — was peak tween-age exuberance, a moment when color-blocking was king and the fashion consensus was "the brighter, the better." It was fun, loud, and very much of its time. But like all neon phases, it eventually fizzled out. At least, that is, until fashion inevitably decides it's time to glow again.

"Mary-Kate and Ashley matching" has become the sartorial shorthand for harmonizing outfits with your friends: in sync, but not identical. It's a fine line between fashion-forward coordination and the mild horror of showing up to the function in a look that matches someone else's exactly. Sasha and Malia are a case in point, both wrapped in mustard-yellow sarongs tied at the waist.

Interestingly, unlike her sister, Malia opts for a slightly oversized graphic tee, a choice that has ebbed and flowed through fashion. According to vintage American clothing brand P&Co, its roots trace back to World War II, when US military members were issued plain T-shirts stenciled with the names of their units, bases, and training programs. After the war, these tops transitioned into casual civilian wear, as seen in their explosion in the 1960s counterculture movement, as well as the logo-heavy skate, surf, and streetwear era of the 1990s.

Today, a graphic tee can go one of two ways: totally cool, elevating an outfit with personality and edge, or painfully tacky, like something scooped up from the dregs of a Forever 21 clearance rack.

If Tumblr in the mid-2010s had an official uniform, the black choker would be the badge of honor. Once thought the height of cool, now there's no mistaking the era it came from. In 2016, when Sasha Obama accompanied her parents to the National Christmas Tree Lighting in Washington, this thin strip of fabric had been worn by every It Girl who had ever reblogged a grainy photo of coffee and Doc Martens.

The boxy fit of the plush navy jacket confirms her '90s influence, with the choker adding another layer to the era's signature grunge aesthetic. This is not to say the look itself doesn't hold up; it's just a reminder that trends move fast. 

For as long as she's been the spearhead of Vogue, Anna Wintour has dictated the rules of fashion. Hemlines rise and fall at her discretion and silhouettes are sanctioned, while color trends are anointed or dismissed with the flick of her signature bob. The color black, as she has ruled, comes with its conditions. In an episode of Vogue's "Go Ask Anna" series, when asked how to elevate an all-black outfit, she said: "Don't wear all black. It seems too gloomy, as if one is going to a funeral." The Obama sisters didn't seem to get the memo. The pair was spotted in Los Angeles — where they moved in 2022 — in athleisure ensembles that were both head-to-toe black.