10 Celeb Outfits That Were Branded Worst-Dressed At The Time But Are Iconic Now

Landing on the worst-dressed list is a rite of passage for A-listers. Even the most fashionable stars have been slammed for their outfits, and while the criticism might stand for a long time, there are times when hindsight changes the general consensus. It might not happen for years, but some ensembles that were once branded "worst-dressed" are later considered iconic.

Fashion ebbs and flows, and what we hate during one stage of life might be something we treasure later on. So it's easy to see how some celebrity outfits aren't warmly embraced off the bat, but then grow on people as the years go on. Often, this happens when a look is ahead of its time. The world might not have been ready for Celine Dion's experimental styling at the 1999 Academy Awards, but looking back, we finally get it. Or an outfit might hit the wrong aesthetic notes at the time, but have an influence over future sartorial trends and shifts that can only be appreciated later. Then there are those outfits that truly embody a star's unique, inimitable sense of style, and we can only appreciate the magnitude of that once we have the chance to step back. Lady Gaga's iconic meat dress is a good example of a look that critics could only come to accept with time to digest it — metaphorically speaking. 

The following stars were trashed for these 'fits, but on review, they were actually pretty monumental. Luckily, they never became red carpet outfits that these celebs had to regret. 

Celine Dion made waves at the 1999 Oscars when she turned up in a suave Dior white suit. The "problem" that, as Vogue recalls, landed her on several worst-dressed lists? She wore the suit backwards. 

But despite the backlash, the "My Heart Will Go On" hitmaker has no regrets. "The only thing I have to say about that is, if I had to do it again, I would do the exact same thing," she confirmed to W magazine in 2007. The world has come to agree with her, with the court of public opinion now considering this suit iconic. 

When Beyoncé graced the red carpet at the Golden Globes in 2007, she took the fashion brief seriously. But despite being appropriately gilded in a jaw-dropping metallic Elie Saab gown with a thigh slit and super-plunging neckline, she ended up on People's Globes 2007: Best & Worst Dressed list as one of the worst. 

However, looking back, several outlets have nothing but nice things to say about this unforgettable 'fit. Harper's Bazaar called it one of "the best Golden Globes dresses in history," while W magazine included it as one of the definitive style moments of Beyoncé's red carpet journey.

When Gwyneth Paltrow walked the red carpet at the 2002 Oscars, the reception wasn't all positive. Actually, it wasn't positive at all. Several critics slammed her Alexander McQueen look, which featured a sheer bodice with a heavy vampy skirt. Today notes that the experimental 'fit ended up on worst-dressed lists, accompanied by descriptions like "the worst dress ever" and "fashion disaster," while People added it to its list of Scariest Oscars Fashions Ever in 2004. 

But over 20 years later in 2023, Vogue celebrated when Paltrow's daughter Apple Martin tried on the dress: "Regardless, it's great to see mother and daughter connecting over an invaluable piece of fashion history embedded with pop culture significance."

Pamela Anderson was the epitome of turn-of-the-millennium style, embracing the most maximalist and overtly sexy aesthetics of the '90s and the '00s in her heyday. Her look at the 1999 VMAs was her signature, featuring a white corset, blingy rose-gold pants, and a furry hat. "I remember her being on every worst dressed list that month for this outfit ..." one Redditor recalled. 

However, Anderson and her style have aged like fine wine, and now the world appreciates her unique take on fashion like they should have back then. In 2023, People called this outfit one of "Pamela Anderson's most iconic looks of all time." 

Rihanna's stunning style transformation has shown that the star has never shied away from taking fashion risks. Compared to some of the looks in her "Rated R" era, the Giambattista Valli Haute Couture pink dress she wore to the 2015 Grammys was quite tame. Unfortunately, E! News referred to the flouncy number as one of its worst-dressed looks of the night. 

Beauty is in the eye of the beholder, of course, but we thought Rihanna slayed in this standout look, and in 2026, People included it as one of the star's best looks ever.

In 2004, Diane Keaton took a major fashion risk by attending the Oscars in a suit, complete with pin-striped pants and a morning coat. Even though Julia Roberts had worn an oversized men's suit to the 1990 Golden Globes, Keaton's take had critics clutching their pearls, and People included it on its Scariest Oscars Fashions Ever list that year. 

But following the "First Wives Club" star's death in October 2025, The Hollywood Reporter named this very look as one of her most iconic. Keaton always had the fashion prowess of an it-girl, even if the world didn't always appreciate it.

Throughout the history of modern fashion, no dress has been parodied like the swan dress. Worn by Icelandic singer Bjork to the Oscars in 2001, the dress landed on pretty much every worst-dressed list at the time (via CNN). The Marjan Pejoski tulle creation, shaped like a swan and coming complete with its own eggs that Bjork dropped down the red carpet, became a Halloween staple and a recurring joke. 

However, in October 2024, Harper's Bazaar included it on its list of The 50 Most Iconic Looks of All Time. Who's laughing now?

In 2015, Taylor Swift was riding the waves of her "1989" era. In sharp contrast to her later "Reputation" phase, she was all about color with this album, notably wearing a teal ombré dress by Elie Saab with a full skirt and generous slit that showed off her purple shoes. Unfortunately, fashion blog The Fashion Tag simply said, "Hated it." 

But not everyone agrees. A decade later, Byrdie seemed to think this was a pivotal moment in Taylor Swift's stunning style transformation.

The Christian Lacroix milkmaid dress that "Kill Bill" star Uma Thurman wore to the Oscars in 2004 ruffled more than a few feathers at the time. It landed on People's Scariest Oscars Fashions Ever list that year, drawing comparisons to classic Swiss character Heidi. 

Interestingly, Thurman was actually trying to be named "worst-dressed," because that would mean standing out. "Everyone had it down to such a perfect tee in their spaghetti-strapped, sequined or chiffon, body-hugging, gym-hour promoting things," she told THR, per Evoke. "You get bored." It wasn't until 2026, over 20 years later, that Dazed called this experimental outfit "an iconic fashion moment." 

Fashion critics weren't kind to Kate Hudson after the 2001 Oscars, when the star walked the red carpet in a silver-purple Stella McCartney backless gown with a high-neck fringe capelet. "I got trashed for this dress," Hudson recalled in a 2023 TikTok video. "I got on every worst-dressed list." Hudson added that looking back, she loves the dress. 

In 2026, L'Officiel backed up the "Almost Famous" star's opinion, noting that in hindsight, the dress was a trailblazer, paving the way for the transition from red carpets full of traditional eveningwear to those with creative, intentional, and dramatic designs. 

Next, check out these Oscars dresses from the 2020s that are destined to be in the hall of fame.