Oscar Holland, CNN

This week marks two decades since Hollywood served up one of its worst-received red carpets of all time. On a night of big wins for “A Beautiful Mind” and the first “Lord of the Rings,” 2002’s Academy Awards were — in true Y2K style — awash with spaghetti straps, visible midriffs and shapeless eveningwear.

At the time, former Cosmopolitan editor Marcelle d’Argy Smith branded it a “night of fashion blunders,” before calling out several stars for their efforts. Julia Roberts, in a black Armani gown, looked “boring”; Whoopi Goldberg, who hosted the ceremony dressed like a glittering peacock, brought “a kind of circus element to the proceedings”; and Barbra Streisand was “swathed” in a velvet burgundy “wrap/tent/curtain.”

More damming reviews were saved for the year’s best supporting actress, Jennifer Connelly, who opted for a dishwater-colored tulle gown and not-quite-matching scarf (a shade described by Smith as “pale dung-colored,” and by Scripps Howard news agency as “phlegm-colored”). Elsewhere, Cameron Diaz divided opinions in a floral print dress, ’80s Oscar-nominee Sally Kirkland sported an ill-advised bejeweled bindi and Faith Hill took a painfully literal approach by teasing her performance of “Somewhere Over the Rainbow” with a strappy rainbow-colored Versace gown.

The night will, however, always be remembered for one of the most maligned outfits in Oscars history: Gwyneth Paltrow’s infamous “goth” dress (pictured top). The formless Alexander McQueen creation featured a scrunched-up taffeta skirt and sheer bodice that left little to the imagination. The actress’ heavy eye makeup and milkmaid braid helped secure the outfit’s place on “worst-dressed” lists for years to come.

In a characteristically cutting review of the evening’s looks, long-time Vogue editor Suzy Menkes, then of the International Herald Tribune, wrote that the evidently bra-less Paltrow “looked like she was off to see her personal trainer.” (She also described Connolly as being “drear as a drowned nymph”). The Guardian’s fashion writer Jess Cartner-Morley meanwhile wrote that the star “came a cropper” in “gap-year plaits, goth eye make-up and clunky jewelry.”

There was, arguably, worse to come. At the Vanity Fair afterparty, “Meet Joe Black” star Claire Forlani wore what can only be described as a sequined breastplate held up by perilously thin string ties; Selma Blair arrived in a barely-there fringe dress that looked more like a shabby tablecloth and Heather Mills opted for a bizarre midriff-bearing two-piece. Actress and author Suzanne Somers’ dress might easily have doubled up as cheap curtains, and TV host Daisy Fuentes showed up in jeans and a blouse, as if she had forgotten it was one of Hollywood’s most exclusive parties.

Most boring ‘of all time’

What really irked fashion critics was not the well-intentioned flops, but the collective lack of ambition. Just a year after Björk’s unforgettably eccentric swan dress, 2002’s red carpet felt like a meek, low-risk affair.

This may have been for good reason. Held just six months after the 9/11 attacks, the event was engulfed by hyped-up security and an understandably restrained atmosphere. Armed police stood guard, stars were sent through metal detectors and fashion-watchers who were lucky enough to secure a seat on the red carpet had to undergo new background checks, the LA Times reported. In keeping with the national mood, numerous stars arrived in respectfully low-key gowns, with Reese Witherspoon, Glenn Close, Helen Hunt and Renée Zellweger among the many celebrities to wear black that night.

This was no excuse for Menkes, however. Calling attendees’ efforts “the most boring Oscar outfits of all time,” the critic singled out Naomi Watts’ unadventurous corseted dress from a “sea of black,” writing that “even Gucci, usually a dead cert for sexy clothes” had made the star look “sedate.”

Samantha Critchell, then a fashion writer for the Associated Press, was more diplomatic, describing the evening’s red carpet as one of “conservative” fashion on which “many stars played it safe.” Looking back, 20 years on, she attributed their style choices not to 9/11, but to trepidation surrounding the surging interest in red carpet style.

“In the early 2000s, fashion became a microcosm for the rest of the world,” she told CNN in a phone interview. “I started covering the red carpet with Jennifer Lopez’s how-did-it-stay-closed Versace gown (at the 2000 Grammys) — we didn’t do ‘night-of’ coverage of the fashion in the ‘hard-news’ media until that moment.

“There became a realization that those dresses were going to define you. And I think it had more to do with the rise of fashion as a pop-culture force — and a real-time force — and realizing that people were sat at home judging these outfits.

“There was no E! and no pre-show until then, and I think that choices were probably safer because of not knowing how to navigate that.”

As for the riskier looks, Critchell theorized that many celebrities were “playing against type” by offering something unexpected or different from previous outings. Nicole Kidman’s frilly pink Chanel gown contrasted with the elegant chartreuse Dior dress she famously wore to 1997’s ceremony, while Jennifer Lopez’s classic gown and bouffant hairstyle was juxtaposed against the raunchier looks she’d become known for.

Even Paltrow’s outfit can be seen as an attempt to avoid being pigeonholed, Critchell said. “She had been the princess a few years before (in 1999) in that pink Ralph Lauren dress, and I think she was playing against that,” she added.

“Celebrities didn’t have a chance to show their other sides in the way they do now. You already know them, you what their style is, you know their opinion on everything. But it wasn’t uncommon in 2002, or any of those other (pre-social media) years, for someone to play against what they did before, because they didn’t want to be stereotyped.”

Rays of hope

There were a handful of hits amid the flops that night. Kate Winslet’s one-shouldered Ben de Lisi dress was widely praised, and the evening’s men fared better among critics, with Will Smith praised for his Ozwald Boateng suit and gold tie.

There was really only one winner, though — on both the red carpet and the awards stage. On her way to becoming the first Black woman to claim the Academy Award for best actress, Halle Berry stunned in gown that transformed the fortunes of its designer, Elie Saab. Like Paltrow’s outfit, it consisted of sheer top and taffeta skirt, though Berry oozed glamour in crimson and champagne, with strategically placed floral detailing completing the look.

“I think Halle Berry’s outfit has stood the test of time,” Critchell said. “It’s not a dress someone would wear today, but she was the belle of the ball. She was predicted to win and, as fashion writers, we were all waiting for her turn. It fulfilled the moment; it was memorable, and it was right for a best actress.”

Yet, while the outfit is now considered among the Oscars’ best-ever looks, it wasn’t a hit with everyone on the night. The Guardian’s Cartner-Morley wrote that Berry’s outfit, complete with its “gaudy embroidered net bodice,” had offered “plenty to cringe about.”

Her contrarian take serves as a reminder that good red carpet style is in the eye of the beholder — and thus the question of whether 2002 was the Oscars’ worst year depends, as ever, on who you ask. Indeed, given the current interest in all things Y2K — a revival that has heralded the return of low-rise jeans, crop tops and butterfly clips — the power of hindsight (and the opinions of Gen-Z fashion-watchers) may be kinder to 2002’s outing than one might expect.

“I don’t think it was the worst-dressed,” Critchell said. “I don’t know if there would ever be a moment you could define as that. But it was a different time.”

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