Will 2000s “Bad” Fashion Make Its Comeback in 2021?

Silky dresses. Going-out tops. Square-toed boots. Sequins. Newsboy caps. Glittery pink. Dark denim.

The trappings of 2000s fashion are making their way back, predictably, affirming that clockwork idea that fashion works in a 20-year trend cycle and what goes around will inevitably come back around again, two decades later, for better or for worse.

Style stars like Bella Hadid, Hailey Bieber and Dua Lipa — three of fashion’s biggest ambassadors today — regularly sport things like silky camis, hair tendrils, low rise pants — and yes, even that dreaded whale tail, which is already on track to be an a real-life trend for 2021.

Are we ready for it all?

The answer to that question might depend on your age.

“I wouldn’t be caught dead in that again,” was the statement that periodically came from my mother while growing up, whenever I would show her new trends I wanted to try — many of them from the 70s, when she was a teenager. With every flared leg jean, crop top, jumpsuit or pair of platform loafers, I would shrug and wear them anyway, convinced that what I was putting together was fresh, novel and completely in fashion for the moment.

On the other side of it, of having lived through the trends once, repeating them seems to come with a nuanced set of baggage. It’s not just memories of what you were doing when you were wearing them (though that is certainly important). It’s the 20/20 hindsight of it all.

bella hadid, bella hadid fashion, 2000s fashion, 2000s style, 2000s bad fashion
Bella Hadid with a friend in New York City in August 2020. Both are wearing low rise pants, a key silhouette of early 2000s fashion.
CREDIT: Splash

Can Uggs with denim miniskirts, flip flop sandals on the sidewalks, how-low-can-you-go rises, bedazzled trucker hats and platform stilettos really find their way back into the fashion ether?

If fashion has taught us anything over the past decade — with its ’90s-inspired normcore, “dad” shoes and “ugly” sandals — it’s that beauty is in the eye of the beholder. And what bad fashion might be to one person or generation could very well read as novelty to another.

“I’ve found that the way I trend forecast is basically, ‘Am I repulsed by this?’ Ok, then Balenciaga will probably make it in a season or two,” said Gabriel Held, a Brooklyn-based stylist and vintage fashion dealer, known for purveying some of the more adventurous pieces that the two decades had to offer.

Held’s fashion archives (which are available only for rent, primarily through his styling services) also live through his social media accounts, where he’s curated galleries of his #unsungsheroesoffashion — momentarily forgotten ’90s and ’00s-era stars such as Faith Evans, Mya, Rose McGowan and Jamie Lynn Sigler, at the height of their careers wearing looks that distill and pinpoint the trends of the time.

“I’m hesitant to say that there is even such a thing as bad fashion,” said Held, who also uses term “fashion faux-positive” on his Instagram account. “If you go back to (stylist) Misa Hylton, Lil’ Kim’s 1999 MTV VMAs look was largely on the worst dressed list, and it even appears on worst dressed of all time lists. And yet it’s one of the most iconic red carpet looks of all time.”


The rapper’s nipple pasty and coordinating sequined jumpsuit could have been seen as campy, but Held is careful to separate the idea of risk-taking fashion with camp. “There was a lot of confusion, a lot of people thought kitsch was camp,” Held said of the 2019 Met Gala, which celebrated Susan Sontag’s 1964 essay on the idea. “Awareness is crucial,” he added. “To me, camp is inherently intelligent, it’s deliberate.”

The stylist also noted that as trends come back around, there will always be those who are still wearing the pieces, oblivious to the cycle. “Daring people will go for a 10-year revival, and if you’re really daring you would pull out a grotesque Christian Louboutin stiletto with a platform in the front, an Hervé Léger bandage dress, like a bottle service girl.”

While other generations may have scoffed at repeating the looks of their youth, millennials might be the ones best primed for a redux. Nostalgia has been a way of life for the generation, brought to bear by social media itself, in its #TBTs, #FBFs and an endless supply of Buzzfeed listicles that look back on everything from the after-school snacks ’90s kids ate to the butterfly clips that pre-teens wore to school dances at the turn of the century.

avril lavigne, 2000s fashion, 2000s bad fashion, bad fashion, avril lavigne 2000s
Avril Lavigne at the 2002 MTV Video Music Awards.
CREDIT: Splash

Lately, Held has had clients show a nostalgia for early-aughts style stars like Avril Lavigne and the aesthetics of the Disney Channel, whose mid-aughts stars such as Miley Cyrus and the Jonas Brothers have maintained and reignited their own careers.

The best — and worst — of the aughts might also be coming back at just the right time, as fashion and cultural experts alike have predicted the 21st-century version of the “Roaring Twenties,” an explosion of movement, creativity and all-around joie de vivre that seems destined for post-pandemic life.

“2000s fashion was about individuality. There was a lot more freedom, a lot more individual expression,” said Held. “It was more fun, definitely. I think we are edging back towards that.”

imbox Sponsored

Customer Experience, Revenue Stream and Sustainability Come Wrapped in an IMBOX

Sustainable, footwear protection technology company, IMBOX Protection, is bringing its in-store service to the U.S. market for increased foot traffic and basket size with a new revenue stream.
Learn More

Access exclusive content