Ginger Rogers’ Sheer Lace "Lingerie" Look Caused Quite the Stir in 1941
Ginger Rogers won Best Actress for Kitty Foyle, but it was her dress that truly sparked conversation. She wore a dark silk gown with a sheer lace top that some critics at the time felt was a bit too close to "negligee" territory. While it was undoubtedly elegant, the transparent nature of the lace bodice was quite daring for 1941. Allegedly, some conservative attendees whispered about the choice.
But Ginger wore it with such confidence that it became a landmark moment for stars pushing the boundaries of what was considered "appropriate" evening wear for a leading lady.
Ingrid Bergman’s Minimalist "Suit" Style Paved the Away for Starlets to Ditch Costume Gowns for Personal Style (1945)
Ingrid Bergman was never one for excessive fluff, and her 1945 Oscar look proved it. She wore a very simple, dark tailored dress that almost resembled a formal suit, reflecting the utilitarian "Make Do and Mend" spirit of the era. While some expected more "sparkle" from a Best Actress winner, Ingrid’s choice was hailed by others as a refreshing display of authenticity. This look reportedly helped shift the red carpet away from strictly "costume" gowns.
Stars started inching toward a more personalized sense of style, showing that a woman’s talent should always be the main event.
Barbra Streisand's Scandalously Sheer Pantsuit (1969)
This is the "What were they thinking?" moment that defined a decade. When Barbra Streisand won for Funny Girl, she stepped onto the stage in a sequined, wide-legged pantsuit by Arnold Scaasi. The problem? Under the bright stage lights, the fabric became almost completely transparent. Barbra reportedly had no idea it was see-through until she saw the photos the next day. It scandalized the more conservative viewers.
But it also turned her into a fashion rebel overnight. It was a bold, accidental statement on transparency that people are still talking about fifty years later.
Cher’s Groundbreaking Dress Was the First of Its Kind (1974)
Long before the "naked dress" trend of the 2010s, there was Cher. At the 1974 Met Gala, she arrived in a Bob Mackie creation that was essentially sheer mesh with strategically placed white feathers and sequins. It was a jaw-dropping departure from traditional formal wear. While some critics allegedly called it "undignified," it became the blueprint for Cher’s entire fashion legacy. It showed that she wasn't just a singer.
She was a walking piece of art. It remains one of the most daring and influential red carpet moments of all time.
Jane Birkin's Crochet See-Through Dress - Which She Wore Backwards for a Plunging Neckline
Jane Birkin was the ultimate "cool girl" of the 60s, and her appearance at a Paris gala in 1969 proved it. She wore a white crochet dress that was entirely sheer, and in a move that baffled and delighted fashionistas, she wore it backward to create a plunging neckline. She reportedly cinched the front with a brooch and carried her signature wicker basket. It was the height of "boho-chic."
Scandalized traditionalists who were used to stiff corsetry. It remains a symbol of the free-spirited, effortless style that defined the era.
Raquel Welch’s Blue Sequin Catsuit Scandalously Brought Disco Style to a Room Filled With Gowns (1979)
Raquel Welch brought the disco era to the red carpet in 1979 with a royal blue sequined catsuit by Loris Azzaro. It featured a plunging neckline and a skin-tight silhouette that left nothing to the imagination. In a room full of flowing gowns, Raquel looked like she had just stepped off the dance floor at Studio 54. It was a "for better or worse" moment because it was so aggressive in its modernity.
But it perfectly captured the high-energy, high-glamour transition into the 1980s. She looked absolutely electric.
Diane Keaton Shattered Every Red Carpet Rule by Wearing a Suit and Tie to the Oscars (1976)
Diane Keaton broke every red carpet rule when she showed up to the Oscars in a white suit, a vest, and a tie. This "androgynous" look was a direct reflection of her character in Annie Hall and her personal style. At a time when women were expected to be in sequins and tulle, Diane’s "menswear" choice was a shock. Some critics allegedly thought she was being disrespectful to the event, but history has judged her kindly.
She proved that style isn't about following rules; it's about being yourself, even on the biggest stage.
Dolly Parton’s "Barbiecore" Cowboy Suit Drew Lots of Criticism but Was an Early Lesson on Branding and Marketing (1977)
Long before "Barbiecore" was a term, Dolly Parton arrived at the Grammys in a bubblegum pink, rhinestone-encrusted jumpsuit with bell-bottoms. It was loud, proud, and completely Dolly. While the fashion elite of the time reportedly looked down on her "campy" style, this outfit is now viewed as a masterclass in branding. She took the "What were they thinking?" question and answered it with a smile.
She proved thatthat being "too much" is sometimes exactly the right amount. It’s a joyful, sparkly reminder that the red carpet should be fun.
Lauren Hutton’s Pastel Rainbow-Fur Combination Was Ahead of Its Time (1975)
Model Lauren Hutton brought high-fashion "cool" to the 1975 Oscars in a Halston gown that featured a pleated, pastel rainbow skirt. But the real talk of the night was the massive fur coat she draped over her shoulders. It was a look that screamed "New York City chic" in the middle of Hollywood. While some found the fur-on-top-of-rainbow-pleats to be a bit chaotic, it is now celebrated for its "unbothered" elegance.
Lauren looked like she was having the best time, proving that a red carpet is just another place to show off your personality.
Bette Davis’s "Dark Angel" Look Was Shockingly Gloomy for the Time (1955)
Bette Davis was never one to play it safe. At the 1955 Oscars, she wore a dark, heavy gown with a structured collar that framed her face like a dramatic portrait. It was a "villainous" take on glamour that stood out in a sea of sweet, pastel dresses. Some reportedly found it "gloomy," but Bette was sending a message: she was a serious actress, not a doll. This look is still talked about for its sheer intensity.
And for the way it used fashion to reinforce her "legend" status. She was truly a one-of-a-kind presence.
Diana Ross Scandalously Wore Pants to the Oscars (1973)
Diana Ross lived up to her legendary status at the 1973 Oscars in a shimmering gold satin pantsuit by Bob Mackie. It featured a matching waist-length jacket and high-waisted trousers, all in a brilliant metallic hue. She looked like a trophy herself. This was a "for better or worse" moment because it was so flashy and "unconventional" for the Academy, but Diana wore it with such poise that she looked like royalty.
It was the ultimate "diva" moment, showing that a woman in pants could be just as glamorous as a woman in a gown.
Cher’s Revealing "Egyptian Goddess" Look Had Everyone Talking (1973)
Cher and Bob Mackie were at it again in 1973. She wore a two-piece outfit that featured a tiny bra top and a low-slung skirt, all heavily beaded with Egyptian-inspired patterns. It was the ultimate "look at me" outfit. Critics at the time were reportedly divided—some loved the artistry, while others thought it was too revealing for a formal event. Regardless of the opinions, it became a permanent part of fashion history.
Cher proved that the red carpet wasn't just for dresses; it was for making a statement that nobody would ever forget.
Jayne Mansfield’s Infamous Dress Worn to Steal Attention From Hostess Sophia Loren (1957)
While technically a dinner party rather than a formal award show, this moment remains one of the most famous fashion scandals of all time. Jayne Mansfield arrived in a pink satin gown with a neckline so daringly low that it reportedly led to a "wardrobe malfunction" during the meal. The event was a welcome dinner for Sophia Loren, and the resulting photograph—showing Sophia glaring directly at Jayne’s bodice—became an instant classic.
Sophia later admitted she was terrified that Jayne’s dress wouldn't stay in place. It remains the ultimate example of a star using fashion to steal the spotlight from their host.
Carroll Baker’s Sheer Scandal Had America Gasping (1964)
Long before the term "naked dress" was a household phrase, actress Carroll Baker caused a massive stir at the London premiere of The Carpetbaggers. She wore a Pierre Balmain gown that was essentially a nude-colored silk sheath topped with entirely transparent lace. It was so revealing for 1964 that it reportedly caused a near-riot outside the theater. Police allegedly had to step in to manage the crowds who were desperate to get a glimpse of the star.
It was a calculated move to promote her "bombshell" image, but it nearly backfired when the more conservative press labeled the look "indecent."
Edy Williams’ Leopard Bikini and Fur Coat Had Everyone Talking (1974)
If you want to talk about "What were they thinking?", you have to mention Edy Williams. She made a career out of crashing the Academy Awards in outfits that were barely there. In 1974, she arrived on the red carpet wearing a tiny leopard-print bikini and a massive fur coat. She reportedly dropped the coat for photographers, leading to a spectacle that overshadowed many of the actual nominees.
While she was never a major award contender, her ability to hijack the red carpet with "outrageous" fashion made her a staple of gossip magazines for years. It was the ultimate 70s publicity stunt.
Cher’s Revenge on the Academy: Her "Mohawk" Ensemble (1986)
Though slightly outside the 70s window, this look is the spiritual successor to her earlier boundary-pushing gowns. After reportedly being told by the Academy that she wasn't a "serious" actress, Cher showed up to present an award in a Bob Mackie creation featuring a black jewel-encrusted loincloth, a midriff-baring top, and a two-foot-tall feather mohawk. It was a glorious "middle finger" to the establishment.
Some critics allegedly called it a "Halloween costume," but Cher had the last laugh when she won an Oscar herself just two years later. It remains the gold standard for using fashion as a weapon of defiance.
Rita Hayworth’s Premiere Gown That Had Censors Sweating With Nerves (1946)
While Rita Hayworth was known for her onscreen smolder, she brought that same energy to the red carpet in a way that reportedly made censors nervous. She wore a black, strapless Jean Louis gown that echoed her famous "Gilda" costume, featuring a high side slit that was quite daring for the mid-1940s. At a time when red carpet fashion was often quite modest and structured, Rita’s embrace of her "femme fatale" image was a shock to the system.
It was a groundbreaking moment that showed stars could use their public appearances to reinforce their cinematic brand, even if it ruffled a few conservative feathers.
Joanne Woodward’s $100 Homemade Gown Offended Hollywood (1958)
When Joanne Woodward won Best Actress for The Three Faces of Eve, she did something that left the fashion elite completely baffled: she wore a dress she had designed and sewn herself for about $100. The dark green satin gown was simple and elegant, but the fact that a major star would "DIY" her Oscar look was seen as a major scandal. Joan Crawford allegedly remarked that Joanne was "setting the fashion industry back twenty years."
It was a groundbreaking moment for "authenticity," showing that talent didn't need a designer price tag to shine, even if the industry wasn't quite ready for it.
Marisa Berenson’s Sheer Halter at the Met (1974)
Marisa Berenson, the "it girl" of the 70s, arrived at the 1974 Met Gala in a look that defined the decade's obsession with freedom and light. Her halter-style gown was made of a fabric so thin and gauzy that it was virtually transparent under the flashbulbs. In the glamorous, dimly lit halls of the museum, she looked like a shimmering statue. While some socialites allegedly found the look "indecent," Marisa’s confidence turned it into a high-fashion triumph.
It was a "What were they thinking?" success that helped shift the evening-wear trend toward the "barely-there" aesthetic that Halston and his contemporaries made famous.
Demi Moore’s DIY Spandex Bike Shorts (1989)
Demi Moore decided to skip the professional designers for the 1989 Oscars and famously co-designed her own ensemble. The result was a "Frankenstein" of fashion: a metallic floral corset, a voluminous open-front skirt, and—most shockingly—a pair of spandex bike shorts trimmed in lace. In an era where the Oscars were still strictly "ballgown only," the sight of athletic wear on the red carpet was a total system shock.
Critics allegedly used it as the prime example of why stars need stylists, but Demi’s "moxie" made it one of the most discussed outfits of the decade. It was a "What were they thinking?" moment that has since gained a cult following for its sheer 80s bravado.
Cindy Crawford’s "Red Hot" Versace Plunge Ushered in the Supermodel Era of Red Carpets (1991)
When supermodel Cindy Crawford attended the 63rd Academy Awards with Richard Gere, she didn't just walk the carpet; she set it on fire. Her bright red Versace gown featured a neckline so deep it reportedly made the broadcast censors sweat. While it was undeniably beautiful, the "scandal" was the sheer level of bombshell energy it brought to a historically stuffy event. It was a groundbreaking moment that officially ushered in the "Supermodel Era" of the red carpet.
The person wearing the dress became just as much of a star as the actors being honored. It remains the gold standard for a "red dress" moment.
Elizabeth Hurley’s Dress Held Together by Safety Pins (1994)
Elizabeth Hurley went from being "Hugh Grant’s girlfriend" to a global household name in a single night thanks to one Versace dress. Held together by oversized gold safety pins along the side, the gown featured daring cutouts that left very little to the imagination. Allegedly, it was the only dress left in the Versace press office for her to borrow. The "scandal" was its sheer audacity.
Many felt it was "too lewd" for a film premiere, while others hailed it as a masterpiece of neo-punk glamour. It’s perhaps the most famous example of a dress creating a career out of thin air.
Lizzy Gardiner’s American Express Gold Card Gown (1995)
Costume designer Lizzy Gardiner took "on-theme" dressing to a literal extreme when she attended the Oscars in a dress made entirely of 254 expired American Express Gold cards. The cards were joined by wire to create a shimmering, plastic "chainmail" effect. While it was a clever nod to her work on The Adventures of Priscilla, Queen of the Desert, some critics reportedly felt it was a "tacky" publicity stunt.
However, it became one of the most iconic "What were they thinking?" successes in history. It proved that the red carpet could be a place for high-concept art and humor, not just traditional beauty.
Rose McGowan’s "Silent Protest" Naked Dress (1998)
Rose McGowan’s appearance at the 1998 MTV VMAs remains one of the most controversial red carpet moments of all time. She wore a sheer, black beaded "dress" that was essentially a string of beads over a thong. At the time, it was viewed as a pure play for attention and was censored on many broadcasts. However, Rose later revealed that the dress was a "political statement" and a way of reclaiming her body following a personal trauma involving a powerful Hollywood figure.
It was a "Hard to Look Away From" moment that used fashion as a shield and a shout, decades before the #MeToo movement would bring such conversations to the forefront.
Celine Dion’s Backwards Dior Tuxedo (1999)
Celine Dion is a fashion risk-taker, but her 1999 Oscar look—a white Christian Dior tuxedo worn completely backward—left the world scratching their heads. She topped it off with a tilted fedora and sunglasses. The "scandal" here wasn't about skin; it was about the subversion of formal wear. Critics at the time allegedly labeled it one of the "worst dressed" moments in history, failing to see the avant-garde vision Celine was aiming for.
It was a classic "What were they thinking?" moment that has actually aged quite well, now seen as a bold experiment in gender-bending fashion.
Juliette Lewis’s Cornrows and Pearls Combo (1992)
When a young Juliette Lewis attended the Oscars with then-boyfriend Brad Pitt, she chose a look that was as "90s alt-girl" as it gets. She wore a simple, sleeveless white gown but paired it with tight cornrows and a massive, multiple-strand pearl choker. The juxtaposition of the traditional pearls with the edgy hairstyle was a major "What were they thinking?" moment for the old-school Hollywood crowd. Allegedly, some felt the look was "cultural appropriation" or simply too "street" for the Oscars.
Regardless, it became a time-capsule moment for the 1990s, capturing the era's obsession with mixing "high" and "low" culture.
Whoopi Goldberg’s "Disney Villain" Jumpsuit (1993)
Whoopi Goldberg made one of the most polarizing choices in red carpet history when she appeared in a lime green and deep purple brocade jumpsuit. The outfit featured a high-low skirt attached to the back, and the color combination was so jarring that it was immediately compared to a cartoon villain. Whoopi later admitted that the negative backlash "hurt her feelings" and kept her from dressing up for years.
However, in hindsight, many fashion historians see it as a joyful, avant-garde risk that brought much-needed personality to the carpet. It remains a fascinating example of how "originality" can sometimes be met with initial confusion.
Courtney Love’s $20 Thrifted Slip Dress (1995)
Before her high-fashion makeover, Courtney Love arrived at the Vanity Fair Oscar party in a $20 thrifted slip dress, smeared lipstick, and a plastic tiara. She reportedly brought her friend Amanda de Cadenet in a matching outfit, and the pair spent the night being unapologetically loud and messy. It was a "Hard to Look Away From" moment because it flew in the face of the "perfect" Hollywood image.
Critics allegedly labeled her "trashy," but the look actually birthed the "kinder-wh*re" aesthetic that defined 90s grunge. It was fashion as rebellion, showing that you didn't need a designer to be the most interesting person in the room.
Geena Davis’s High-Low "Prom Queen" Ruffles (1992)
At the peak of her Thelma & Louise fame, Geena Davis arrived at the Oscars in a white, tiered dress that looked like a cross between a wedding gown and a 1980s prom disaster. The "high-low" hemline featured a massive, ruffled train that made it difficult for her to move without a small army of helpers. This look is a perennial favorite on "What were they thinking?" lists because it was so aggressively flamboyant.
Allegedly, Geena loved the theatricality of the dress, but critics were less kind, calling it a "fashion fail" of epic proportions. It remains a kitschy, unforgettable symbol of 90s excess.
Cher’s "Moonstruck" Sheer Victory (1988)
After being snubbed for a nomination the year before, Cher returned to the 1988 Oscars with a vengeance. For the night she won Best Actress, she wore a Bob Mackie creation that was essentially a few strategically placed beads on a sheer, skin-toned mesh. It was a "for better or worse" moment that left the audience breathless. While some critics allegedly felt it was "unbecoming" of a serious actress, Cher’s look became the definitive image of her career.
It was a masterclass in transparency and confidence, proving that she could win the industry's highest honor while still refusing to play by its traditional, stuffy rules.