The 10 Most Horrendous Oscar Gowns in History

Snarky "Worst Dressed" lists have ruined red-carpet fashion, driving image-conscious starlets to bland, forgettable couture. But some of the those so-called worst gowns deserve a fresh new look.

As Oscars coverage rolls on, all eyes turn to fashion—and then quickly glaze over as the inevitable parade of safe, beige gowns unfolds. Discerning style lovers sigh, and unreflective tabloid editors ask themselves why, yet again, actress after actress has chosen to dress, unremarkably, in the color of gruel.

The answer is obvious: We’ve forced them to, by labeling any real fashion risk with the dreaded “Worst Dressed” tag. To achieve the sort of lowest-common-denominator “good taste” that pleases InTouch readers and Snuggie owners, anxious stars have formed “a lifeless sea of beige,” as one blogger put it. “When you get right down to it, red-carpet fashion is more plebeian than haute,” said the Miami Herald in a 2007 elegy for idiosyncratic Oscar fashion. “This is an opportunity for stars to register, on their own terms, with the people who eat at TGIF’s.”

Decades of “Academy Awards Gowns Hits & Misses” stories have slowly killed sheer sartorial gutsiness, backgrounded by a long crimson rug. It’s time to revisit—and reevaluate—ten of the so-called “Worst Dresses.” And yes, there will be swans.

THE “NIGHTMARE PAJAMAS”

Barbra Streisand in Arnold Scaasi, 1969

This sparkly amalgamation of sailor suit and negligee lives forever in infamy. Its peek-a-boo factor infuriated traditionalists, but even hipper critics could find no kinder word than “kooky.” The author of a 2003 Variety book seemed to actually fear the ensemble, describing it as “incomprehensible… nightmare pajamas.” If you are under 10, please look away for your own safety.

Viewing the look through the dull prism of contemporary Oscar style, I find it charming in a ballsy Bob Mackie-meets-Rembrandt way. Natalie Portman could pull this off, or someone French and daunting. Or the model who—hair slicked back more chicly—resurrected it for the 2007 fashion show, A Celebration of Oscar Fashion, revealing undetected coolness.

THE “DRAG QUEEN’S CABARET COSTUME”

Kirsten Dunst in Chanel Couture, 2007

Dunst was widely dumped on for this insufficiently boring, neo-Edwardian look. Sixty-two percent of Us Weekly readers “hated” it.

Granted, the dress has its faults. It’s not beige. It’s too virtuosic for A.B.S. by Allen Schwartz to rip off instantly and sell online to depressed dental hygienists. And it’s not formulaically sexy. I regret Kirstin’s hair and makeup, but applaud her for standing there so sweetly knowing she was about to get ripped to shreds. And the juxtaposition of ornate, vampy beading and a modified schoolgirl collar is beautifully apt for a young, but hardly naïve, star.

THE “BRAVE” MUSTARD MISHAP

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Michelle Williams in Vera Wang, 2006

A lot of Monday-morning quarterbacks loved this gown, which is odd since quarterbacks rarely wear tulle. Other critics found the color too challenging, nervously likening it to Kraft Dinner, Big Bird, a “diseased liver,” or a hot-dog condiment: “Pretty Michelle Williams would've been a natural for the neutrals,” wrote one brainwashed beige fanatic. “Instead, she went with a mustard-yellow confection.”

Nonsense. This color is beautiful on Williams, succulently so, and the design itself is a knockout, confidently mixing old-school glam details like starburst ruching with a simple ribbon belt.

THE MONK

Vanessa Redgrave in unknown designer, 1978

Even in the open-minded late-‘70s, when off-duty coal miners could lounge about in kaftans, this dress was savaged. Admittedly, Medieval bell-sleeves are not slinky, but I find Redgrave’s look more intriguing in formal design terms than your average fitted slip-dress: the way its imposing bulk underlines the delicacy of the shoulder ties; the swagger with which its neckline asserts the clavicle region as an alternate erogenous zone. My one complaint: Why is she wearing a watch? A large stone sundial would have been more appropriate.

THE “SWISS MISS”

Uma Thurman in Christian Lacroix, 2004

Here we have the classic example of interesting, cutting-edge fashion that failed to make the cut. Thurman’s gown was too avant-garde for People magazine , which chided her for “billowing” when she could so easily have been “sexy.” Copycat critics invariably invoked Heidi or Switzerland, which I’ve never understood because the white, cerulean blue, and gold scheme looks far more Greek to me, as in Aphrodite, or those Parliament cigarette ads.

I can’t enthusiastically defend the saggy Kimono shape, but the fabric’s translucent, ice-etched effect is lovely, and the discreet accessories are spot-on for an exuberant gown.

Two years later, a repentant Uma wore skin-tight Versace in a meek porridge hue.

THE “LUDICROUS WEDDING CAKE”

Ziyi Zhang in Valentino, 2007

The Memoirs of a Geisha star wore this dress to Vanity Fair’s Oscars party, not the ceremony, but it vexed the Worst Dressed list-makers nonetheless. Primarily because it features “tiers,” which triggered a lot of knee-jerk “wedding cake” remarks. Tiers, it seems, are nearly as criminal as perceived Swissness.

This is not a dress for everyone. It’s a dress for barely anyone. The designer Tory Burch, blonde and overtanned, wore it a few months later and looked like a frazzled prom queen. But Zhang, with her slash of black hair to cut the sugar overload, renders it whimsically pretty in a retro-‘70s way. As for the supposedly clownish tiers, what’s the big deal? They’re a mild variation on an A-line silhouette, and when you’re as dramatically hipless as Zhang, you need some sort of hemline bloom.

THE “BAFFLING” ONE-ARMED MONSTER

Tilda Swinton in Alber Elbaz for Lanvin, 2008

This “velvet Hefty bag” was slammed for lacking a sleeve. It was suggested that Swinton may have misplaced the sleeve. One online critic with a talent for sarcasm expressed concern for Swinton’s unsheathed bicep: “Her poor left arm must be cold with all the wind and rain going on today!”

To which I say: No, she’s not wearing the gown-shaped version of suntan pantyhose that’s become the dreary Oscar norm, but I’d rather see this true original go out on her lonely limb: emphatic, statuesque, uniquely regal, extraterrestrially glamorous. The sack-dress cut, innovated by Givenchy in 1957, is never going to have populist appeal—it’s the antithesis of hot—but neither will Swinton. At least she knows who she is.

THE “FLATTENING” DISASTER

Gwyneth Paltrow in Alexander McQueen, 2002

I was going to take a shot at defending Gwyneth Paltrow’s decision to wear this bleak “undergarment-challenged” number (reportedly egged on by socialite Plum Sykes). I’ve often wondered if the venom that’s been directed at it is a projection of America’s fear of small, droopy breasts. As far as I can tell, the only other person who’s ever tried to see the sunny upside of this “hot goth mess” is Alexander McQueen, who brazenly declared, “She looked incredible.” Anyone care to second that?

THE “OVERWHELMING BOW”

Charlize Theron in John Galliano, 2006

Theron’s decision to don a conspicuous, Gentlemen Prefer Blondes-style bow inspired a lot of melodramatic fretting. It was called a “fatal flaw,” a destructive “bow of doom.” Why hadn’t she had it surgically detached? Only one thing could have made the critics happier: if the bow had attacked and devoured Charlize, punishing her for deviating from the path of bland restraint.

But is it really that bad? To my eye, the weighty dress—with its layered, origami construction and major-statement train—might have looked bottom-heavy without it.

THE “SWAN DRESS”

Bjork in Marjan Pejoski, 2001

Even after eight years, this iconic offense to Oscar propriety is still shrouded in mystery: Is the swan supposed to be dead or just affectionate? Was Bjork consciously spoofing the notion of “swanning about” in finery, or is that giving her too much credit? Is she making a coy allusion to Coleridge’s Ancient Mariner, so famously weighed down with an albatross, to comment on the burden of choosing an Oscar gown? And why couldn’t she find a body stocking with a bit more Spandex?

In any case, it’s everything most Oscar gowns, sadly, are not: unpredictable, unignorable, and beaked. As a dress, it’s not particularly well made. As a spirited refusal to bow down before the forces of banality, it’s a masterpiece.

Dale Hrabi has analyzed culture and trends as a writer and editor for Details, Elle, Radar, and The New York Times. His new humor book, The Perfect Baby Handbook: A Guide for Excessively Motivated Parents, will be published in March.