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.

George Birch / AP Photo 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.

Frazer Harrison / Getty Images 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.

Frazer Harrison / Getty Images THE “BRAVE” MUSTARD MISHAP

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.

Frank Edwards, Fotos International / Getty Images 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.

Frazer Harrison / Getty Images 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.