Outdated Outfits Michelle Obama Has Been Caught Wearing

Society puts a lot of pressure on celebrities (and their stylists) to nail every outfit, whether they're walking the red carpet, attending an interview, or just running errands. We expect their wardrobe to be current, chic, and in tune with each activity. Arguably, there's even more weight put on the fashion of world leaders, who must add adjectives like "modest" and "regal" to this already careful balancing act. So, it's no wonder that a notable figure like Michelle Obama has gotten almost as much press for her closet as for her work.

Like anyone living under the heavy weight of public scrutiny, the former first lady has been called out for many fashion faux pas, including for some inappropriate outfits. But it hasn't all been about pleasing political critics or striking the right chord of formal versus informal. Occasionally, she's suffered a sartorial misstep that has nothing to do with her position and everything to do with timeliness. From her obsession with chunky belts to some questionable throwback styles, Obama has sometimes bamboozled us with her surprisingly outdated looks.

During her husband's stint as President of the United States, Michelle Obama went through a serious sweater obsession. Nearly every public appearance seemed to include a cardigan, whether she was layering it over a formal frock or dressing it down over a T-shirt and jeans. NPR went so far as to call it the "Obama Effect," arguing that Michelle Obama may have single-handedly revived the cardigan look — a style that would go on to dominate the 2010s.

However, it would be pushing it to say that every single cardigan ensemble was a winner. On the contrary, Obama's glut of sweater-based looks sometimes veered into the twee and old-fashioned. For instance, the then-first lady opted for a modest midi dress and cardigan combo while visiting a London primary school in 2009. While we certainly wouldn't have expected sartorial fireworks at a school event, this outfit felt like a dated dud. The blue-and-brown argyle sweater gave off a distinctly Mr. Rogers vibe, and the dress' muted tone lacked any of Obama's usual flair. Completing the look with classy but unexciting pearls, Obama may have been reaching for a vintage Jackie O. feel, but it amounted to more of a Jackie Oh-No.

On another school visit in 2009, this time to Alexandria, Virginia, Michelle Obama once again wore some eye-catching but short-lived styles. This included a dramatic silk blouse, a broad, waist-cinching belt, and her must-have cardigan — all in completely different color palettes.

We understand the Ms. Frizzle-esque intent behind wearing bright clothes to meet young students, but this outfit hasn't held up well over time. On its own, the ruffled, pea-green J. Crew top was a cute, lettuce-like choice for visiting the school's veggie garden. However, it served too much look when paired with the unrelated blue sweater and tortoiseshell-accent belt. Charcoal pinstriped trousers added yet another color and pattern to the mix, creating a displeasing mishmash of aesthetics. While we always appreciated Obama's efforts to model affordable high-street fashions, this look embodied the worst of noughties mall shopping, like she was living through some kind of Charlotte Russe fever dream.

It's also worth noting that the statement belt was hardly an outlier for Obama, whose love for chunky belts seems to come second only to cardigans. Her early first-lady looks often featured a thick belt, whether styled over a dress, blouse, cardigan, or all of the above. There's something to be said for a signature accessory, and sometimes Obama's belts were perfect final touches. But overplaying this style diluted its impact, especially when the belt was unnecessary to the ensemble.

Oh, skinny jeans. What can we say about them that hasn't been uttered a thousand times before? These trousers were the denim du jour of the early 2010s, available not only in typical blue washes but also in an entire rainbow of hues. However, this trend has fallen thoroughly by the wayside, even if some stubborn millennials invite you to pry skinny jeans from their cold, dead hands (er, legs).

Whether you're still pro-skinnies or find them cringey, we have to cast a little side-eye at Michelle Obama's skinny-jean ensemble at the annual White House Easter Egg Roll in 2012. While she chose her denim in a relatively normal indigo hue, the rest of her outfit was a study in eclectic color — almost like she was getting in on the then-popular trend of quirky hipster styling. Fair enough, we could see Zooey Deschanel rocking something similar, from the searingly orange top and mustard-yellow cardigan to the randomly robin's egg blue ballet flats. But it's not an ensemble that would blend in anywhere today.

To make matters worse, even Michelle's daughters, Sasha and Malia, were repping colored skinny jeans at the event — in spring green and sky blue, respectively. This entourage of brightly skinny-jeaned Obama women just shows the style's ubiquity at the time and reminds us that the Obama sisters have also had some outrageous outfits over the years.

Pencil skirts and midi dresses may have been her bread and butter while serving as FLOTUS, but recent years have seen Michelle Obama getting more adventurous in her fashion, including rocking some incredible jackets, shoes, and pantsuits. Obama wore a lot of particularly gorgeous separates during the book tour for her memoir "Becoming" between 2018 and 2019. For example, we're obsessed with the mesh ankle boots she wore in New York and the fringed white blazer she wore in Colorado.

But during the Paris leg of her trip, Obama opted for a more questionable style. Her white-and-orange striped pantsuit looked an awful lot like pajamas, especially with its thick cuffs and satiny finish — a familiarity that couldn't be offset with hoop earrings and strappy heels. We'd call this look outdated, but honestly, was it ever in-date? Too bold and irregular, the suit's pattern didn't quite manage to predict the stripe-centric French girl aesthetic. And while the '70s might have come close to Obama's vibe with some pretty bold leisure suits, her co-ords ultimately look more like Bert and Ernie's bedtime attire than any trend we can remember.

Post-White House hasn't slowed down Michelle Obama. If anything, it's given her the well-earned freedom to explore her passions — and her fashions. This evolution has been fascinating to watch, even when we're presented with the occasional head-scratcher. For instance, in November 2023, Michelle Obama shared a video celebrating the five-year anniversary of "Becoming." In it, the former first lady looked happy and glowing in an ensemble of vivid blue denim. However, as infectious as her energy was, the outfit itself came off as outdated.

The central statement piece of Obama's look was the designer denim jacket with its contrast stitching and leather pocket. A close look at the pocket's embossing reveals the jacket as a Loewe piece sold in various denim shades. Unfortunately, Obama's choice to rock an intense indigo hue and match it with equally saturated jeans dated the garment a decade (or two, or three). Her styling didn't help matters, either. By layering all this pristine denim over a camel turtleneck and adding gold hoop earrings, Obama gave the look a decidedly '90s vibe. It's an outfit that wouldn't have looked out of place on Queen Latifah circa "Living Single," which we kind of love, actually. Still, it doesn't make the look any more modern.

All told, this outfit was a bit of a toss-up. Outdated? With that boxy silhouette and throwback styling, yes. But did Obama still pull it off? Very nearly.