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And the Best Dressed Oscar Goes To… These 5 Groundbreaking Gowns From Academy Awards Past

These looks were definitely winners.


While it’s fun to see who wins big at the Academy Awards, let’s be honest: the best part of the night is seeing what everyone’s wearing. There’s your traditional ball gowns, which are, of course, gorgeous. But what’s really exciting to see are the looks that break the red carpet fashion mold. In the 90-plus years that the annual ceremony has been running, there have been more stunning Oscar fashions than we can possibly count — so instead, we’ve gathered those that stand out for their unexpectedness. Below are five risk-taking Oscar looks and the stories behind them. 

1. When Sharon Stone embraced an off-the-rack shirt.

Actress Sharon Stone at the 1998 Oscars with her husband, Phil Bronstein
Featureflash Photo/Shutterstock

Actress Sharon Stone’s beauty and style wouldn’t be out of place in Old Hollywood., and through the years, she’s shown us how to playfully mix classic glamour with contemporary cool. While today’s red carpet looks are tightly controlled by celebrity stylists and designer partnerships, the Basic Instinct star shook things up in the ’90s when she wore shirts from the Gap to the awards — not once, but twice. 

In 1996, she paired a black Gap turtleneck with a Valentino skirt and Armani tuxedo jacket. This chic and understated look was the result of a stressful delivery mix up wherein Stone’s gown was run over by a FedEx truck; as a result, she was unable to don the custom Vera Wang dress she had planned to wear. Thankfully, Stone and her stylist were resourceful, throwing together a look that mixed designer pieces with an affordable basic. The look was such a success that two years later, Stone paired a long satin Vera Wang skirt with a simple white button-down shirt from — you guessed it — the Gap. The casual shirt (complete with undone buttons and rolled-up sleeves) and elegant skirt was the perfect combination of chic and undone.

2. When Rita Moreno channeled her 1962 self.

Actress Rita Moreno at the 2018 Oscars
David Fisher/Shutterstock

Still going strong at 91 years young, actress Rita Moreno is a living legend. In 1962, she won the Best Supporting Actress Oscar for her role in the musical West Side Story (becoming the first Latina actress to do so), and wore a black and gold gown that was custom made in Manila. Over 50 years later, in 2018, she attended the Oscars wearing the same dress again. Not only was the full-skirted frock in perfect condition, it also still fit her beautifully. 

Moreno’s dress did get one alteration. In 1962, the neckline of the then sleeveless gown covered her collarbone. In 2018, it was strapless. The change — as any woman over 50 will tell you — was bold, as it bared both her shoulders and arms (though she did also wear the elbow-length gloves she’d worn the first time around). Moreno’s commitment to being sustainable (by shopping her own closet) and having fun with fashion was inspiring, and her confidence lit up the night.

3. When Cher dressed for revenge.

Actress and singer Cher at the 1987 Oscars
Eugene Adebari/Shutterstock

Actress and musical icon Cher is the queen of over-the-top fashion. In 1986, she wore one of her wildest looks ever: a skimpy top of sparkling black triangles held up by a complex system of straps, paired with a matching long, low-rise skirt, a floor-length robe, and a feathered headdress. The outfit, designed by her frequent collaborator Bob Mackie, was a sartorial act of vengeance. Cher wasn’t nominated that year for her role in Mask (for which she won Best Actress at the Cannes Film Festival) so she decided to make a spectacle with her look. 

Cher would go on to win Best Actress in 1988 (for her role in Moonstruck), but it was her 1986 feathered fabulousness that we remember best. When she took the stage to present the award for Best Supporting Actor, she quipped, “As you can see, I did receive my Academy booklet on how to dress like a serious actress.” You gotta love a woman who brings wild style and a sense of humor to Hollywood’s biggest night.

4. When Julia Roberts wowed in black.

Actress Julia Roberts at the 2001 Oscars
Stewart Cook/Shutterstock

As America’s sweetheart, it makes sense that Julia Roberts would be all class on the red carpet. When she won her Best Actress Oscar for Erin Brokovich in 2001, she wore a chic black Valentino gown with Y-shaped white strap detailing and a tulle train. According to a recent survey by the British fabric company Dalston Mill, black is the luckiest color for actresses to wear to the Oscars: when looking at the documented dresses worn by every Best Actress winner, they determined that a majority of them were black. Clearly, black is not only flattering — it’s charmed.

Roberts’ black dress indeed proved lucky, and its graceful minimalism was highly influential — the style was particularly beloved by teens, and oft-reproduced in prom dresses of the time. Unlike many other red carpet dresses, this one wasn’t new or custom-made; it was from 1992. Today, wearing “vintage” on the red carpet is a trend. That wasn’t the case, however, in 2001. Roberts and her dress, which has its own Wikipedia page, were ahead of the curve.

5. When Barbra Streisand made a statement in sheer fabric.

Actress and singer Barbra Streisand at the Oscars in 1969
George Birch/AP/Shutterstock

Barbra Streisand’s 1969 Best Actress win for her role in Funny Girl was historic in two ways: She tied with Katharine Hepburn for the award (each star received 3,030 votes), and she wore a truly fabulous outfit. Instead of a gown, she donned a sparkling sheer black pantsuit with a bow, a white collar and cuffs, and some spectacularly wide bell bottoms (hey, it was the ’60s). 

The suit, from designer Arnold Scaasi, was a playful, sexy take on a tuxedo that only a diva like Babs could pull off. In a 2016 interview with W Magazine, she admitted that she didn’t realize how sheer the outfit was until the lights hit it on the red carpet. In those days, pants (especially sheer ones!) at awards shows were a particularly bold move for women. Even if Streisand’s outfit didn’t look how she anticipated it would, she definitely dazzled. 

Happy 95th Academy Awards!

From the understated and elegant to the sparkling and extravagant, these five women all made memorable fashion statements. And we can’t wait to see what kinds of looks our favorite actresses will turn up with this year at the 95th annual Oscars (the ceremony begins Sunday March 12 at 8 p.m. EST, broadcast on ABC and hosted by Jimmy Kimmel). In the meantime, what’s your favorite red carpet outfit? Leave it in the comments.  

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