Cher (1998)

Cher's outfit at the 1998 Oscars was a display of Hollywood glamour and daring. The famed singer and actress had all eyes on her in this sheer white beaded cold-shoulder number with a bent halo headpiece.

The dress itself was a masterpiece of intricate beadwork, pushing the boundaries of convention. But it was the frilly visor and lace choker that truly caught everyone's attention, daring to explore uncharted territory on the red carpet. Cher takes her red-carpet fashion very seriously. Her ultimate aim is to be as dramatic as she can possibly be. In fact, she once mentioned, "I thought we were in show business?" when talking about her outfits.

Kristen Stewart (2022)

At the 94th Academy Awards, Kristen Stewart made a grand entrance on the red carpet, showcasing a modern take on timeless elegance. Wearing Chanel, she confidently combined a sleek suit jacket with black shorts.

While her outfit aimed to make a bold statement, it didn't quite capture the enchanting allure typically associated with the Oscars' red carpet. Nevertheless, it looks like this outfit perfectly reflected Kristen's adventurous spirit and unique sense of style. Although it may have fallen slightly short of the breathtaking visual spectacle that the prestigious event is renowned for, it left the audience yearning for a touch more cinematic glamour.

Emerald Fennell (2021)

We're puzzled by Emerald Fennell's decision to wear a floral Gucci dress to the Oscars. Although it's perfect for a casual brunch with friends, it doesn't quite fit the bill for the grand red carpet.

While the springtime print is beautiful, it may not be the most appropriate choice for such a momentous occasion. It's important to keep in mind that personal style can say a lot, and as a winner of Best Original Screenplay, we were hoping for a more exciting and stunning outfit that truly captures the essence of the Academy Awards because, after all, the Oscars is a glamorous event.

Amanda Seyfried (2021)

Amanda Seyfried, a 35-year-old nominee for Best Supporting Actress for "Mank," looked stunning at the 2021 Oscars in an Armani bold red dress, as it was voluminous with tulle material and a flared bottom, which gave her a commanding presence.

Designed by Giorgio Armani himself, the strapless gown was inspired by hibiscus flowers and resembled Old Hollywood style. However, the dress seemed to overpower her elegance, making it seem like it was wearing her rather than the other way around. The design was ambitious, and while she has worn some good Armani pieces before, this one didn't quite hit the mark.

Laura Dern (2020)

Laura Dern made a stunning appearance on the Oscars' red carpet, exuding the timeless elegance of the late 1990s and early 2000s. Her dress seemed quite simplistic, and many thought it needed a little something extra to truly shine because this light pink color made her look washed out.

However, to our bewilderment, Armani decided to adorn it with a beaded black bra, which also seemed like an unfortunate choice. Although the dress was not the best, Laura, the recipient of numerous accolades, took home that year's Academy Award for Best Supporting Actress for her role in the movie "Marriage Story."

Kim Basinger (1990)

Kim Basinger's 1990 Oscar gown was a bit of a fashion experiment gone slightly awry. It was a combination of a gown and a tuxedo, creating a Frankenstein-like ensemble that definitely caught people's attention.

Adding to the intrigue was the single white glove she wore. Critics had mixed opinions about it, but what many people don't know is that Kim actually designed the white satin creation herself. Considering Kim's status as one of the most beautiful women of the decade, it's safe to say that if she had a trusted style advisor, she might have opted for a different dress and spared us the "innate" tailoring skills.

Demi Moore (1989)

Demi Moore's 1989 Oscars outfit was the stuff of fashion nightmares. Apparently, she came up with this outfit herself and it was as if she'd raided her 1980s workout wardrobe, donning what could easily pass for bicycle shorts, an embroidered corset top, and a bra. Her red carpet style that evening was nothing short of tragic, and the outfit remains a legendary eyesore in Oscar history.

But even though the outfit was deemed in the worst-dressed category, the same hybrid look costs more than $4.5k today. While she's been a Hollywood icon, even Demi couldn't escape the clutches of the occasional style stumble.

Lea Seydoux (2020)

Lea Seydoux looked beautiful at the 2020 Oscars, but we can't say the same about this Louis Vuitton gown. The dress was a collaboration with the Red Carpet Green Dress organization. Lea's custom-made Louis Vuitton gown was designed with sustainability in mind. It showcased a fabric called organic silk faille, which is made from TENCEL Luxe filament yarn.

This fabric is an eco-responsible option that perfectly combines style and environmental consciousness. And her custom-made organic satin sandals were eco-friendly, too. While we appreciate the cause, the dress had a challenging neckline and a puffy disproportionate bottom, which didn't fully complement Lea's natural elegance.

Kacey Musgraves (2019)

Kacey Musgraves, famous for her country music and the iconic motto of her song "Follow Your Arrow," caused quite a stir with her 2019 Oscars outfit, although perhaps not the kind she had hoped for.

In the midst of a sea of extravagant pink gowns that dominated the red carpet that year, Kacey managed to attract attention for all the wrong reasons. She took the pink trend to a whole new level by adorning her dress with adorned bows and what can only be described as tutu bracelets. Ultimately, the dress served as a reminder that sometimes it's best to follow your arrow, but perhaps not towards the costume shop.

Margot Robbie (2021)

Margot Robbie, as radiant as always, made a stunning appearance on the Oscars red carpet in 2021. Her dress exuded botanical elegance, with a touch of silver that added a special flair.

However, it seems like some felt that the gown didn't fully complement her undeniable beauty. The silver accents, meant to elevate the ensemble, subtly resembled plain tin foil, while the floral design lacked the expected glamour for such a prestigious event. Unfortunately, in 2020, a notable stylist included Margot on his 'worst-dressed' list, reminding us of the subjective nature of style and the constant scrutiny faced by Hollywood's stars.

Kristen Wiig (2020)

Kristen Wiig brought her own unique style to the 2020 Oscars red carpet. She wore a bold Valentino dress and paired it with elegant black gloves, creating a distinct and eye-catching look.

However, her choice was met with resistance from some individuals, as it deviated significantly from the norm. Some critics went as far as labeling it the "lasagna dress" due to its unconventional and uncomfortable appearance, characterized by distinctive layering. And, naturally, since it's the internet, there were plenty of memes created on Twitter at the expense of this dress, with truly interesting captions: "Who wore it better: Kristen VS Lasagna?"

St. Vincent (2018)

At the 2018 Academy Awards, St. Vincent, a Grammy-winning artist and now one of the artists in Marc Jacobs' label's F/W 16 campaign, made a statement on the red carpet with what can only be described as an audacious take on the classic little black dress.

Her daring outfit featured a barely-there black minidress, an eccentric puffy sleeve, and a hemline that defied fashion physics. It certainly turned heads and sparked conversation. Some might call it bold, while others might say it was a fashion experiment gone rogue. St. Vincent proved that at the Oscars, anything can happen, and anyone can steal the show.

Salma Hayek (2018)

Salma Hayek made quite the impression at the 90th Academy Awards. Her lavender pleated gown, adorned with a unique diamond chain design on her shoulders, had everyone talking.
The dress's color and cut left fashion enthusiasts scratching their heads, wondering what inspired such a bold choice.

It was undeniably eye-catching, but some couldn't help but question if it was a bit too boring. After all, Salma is known for her natural glamor and doesn't need excessive embellishment to shine. Perhaps this was just a rare style hiccup for the seasoned fashionista. Regardless, her 2018 Oscar dress will definitely be remembered as one for the books.

Andra Day (2018)

Andra Day's 2018 Oscar dress was a display of flowers that caught everyone's attention on the red carpet—it was impossible to overlook. However, being visible doesn't always mean being desirable.

Her extravagant floral print outfit left many puzzled; it was like wearing a garden to a formal occasion. The puffy design gave it a pantsuit feel rather than the elegance expected of an Oscar-worthy gown, and it seemed as if she was swimming in fabric. Ironically, her entire look was excessive, but not in the "extraordinary" way one hopes for at the Oscars. This just proves that even in the glamorous world of Hollywood, sometimes, less is more.

Charlize Theron (2010)

Charlize Theron, the star of "Atomic Blonde," known for her impeccable red-carpet appearances, made a bold move at the 2010 Oscars in a striking Dior Couture creation. However, this gown, a unique blend of pink and purple satin, did not capture the expected elegance of the Academy Awards—especially the part of the chest with two roses.

It resembled a fashion-forward outfit more suitable for the runways of Paris rather than the star-studded Oscars. But when asked about her gown on the red carpet, Theron wasn't offended at all. In fact, she happily shared with the "US magazine" that she loved this dress very much.

Stacy Keibler (2012)

In 2012, Stacy Keibler, the retired professional wrestler, took a bold leap into Oscar fashion territory, but unfortunately, it didn't quite land like a perfect suplex. She chose to wear a Marchesa metallic dress, complete with a noticeable rose on her hip, which many considered to be, well, unattractive.

The oversized floral embellishment garnered more attention than a championship belt, turning it into a fashion mistake that even the toughest wrestlers might cringe at. To add to the peculiarity, her entire ensemble committed the ultimate sin of formal attire—her dress, skin, and hair all shared the same color tone, creating the illusion of a shimmering monochromatic mishap.

Rachel Weisz (2019)

Rachel Weisz, renowned for her fearless fashion choices, graced the 2019 Oscars with her presence in an unforgettable outfit. As a nominee for "The Favourite," she confidently donned a striking red gown with a one-of-a-kind rubber capelet and a pleated skirt with flowers. By pushing the boundaries of traditional red carpet attire, Rachel aimed to make a bold, fashion-forward statement.

However, despite her efforts, the combination, coupled with an additional hairpiece, didn't quite achieve the desired harmony, resulting in a look that seemed slightly out of sync with the event's customary elegance and placed her among the night's most controversially dressed stars.

Linda Cardellini (2019)

Linda Cardellini's 2019 Oscars dress was certainly eye-catching with its bold fuchsia pink color. Yet, as eyes traveled downward, the overwhelming number of frills made it too busy for some.

The mullet hemline added an unexpected twist, with the front cropped short and the back extending into a long, flowing train, but it left a lingering sense of awkwardness. The baby pink bow belt seemed out of place, resembling more of a random bowtie than a thoughtful accessory. Overall, while ambitious, the dress's disjointed elements may not be remembered for the right reasons in the grand scheme of Oscar fashion.

Whoopi Goldberg (2009)

Whoopi Goldberg, the American comedian and actress best known for her role in "Sister Act," made a bold fashion statement at the 2009 Oscars by embracing the leopard print trend.

However, her gown missed the mark with its poor fit, too much animal print detail, and frumpy oversized sleeves. Unfortunately, it seemed like she might have taken the "drowning in fabric" concept a bit too literally. It was definitely a lesson in how not to wear animal print. Despite the trend's popularity, Whoopi's dress was more of a fashion fizzle than a red carpet roar. Nevertheless, it was a memorable experiment in fashion history.

Billie Eilish (2022)

At the 2022 Oscars, Billie Eilish made a daring fashion choice that didn't quite hit the mark. Wearing a voluminous black gown, her ensemble was unfortunately labeled as one of the night's most disappointing looks.

The oversized attire seemed to overpower her petite frame, overshadowing her natural sense of style. However, despite this misstep, Her bold decision once again showcased her non-conformist attitude in the fashion industry. Billie, known for her rapid ascent to fame, has won over fans with chart-toppers like "Bad Guy" and has snagged a handful of Grammy Awards. Her unique sound usually makes her stand out, but this time, her massive gown stole the spotlight.

Jada Pinkett Smith (2022)

Well, it's safe to say that the 2022 Oscars were one of the most talked about Academy Awards. And still, in the midst of an eventful evening, Jada Pinkett Smith made an appearance on the red carpet wearing an emerald Gaultier gown, which was a choice that surprised many because she is known for her stylish red-carpet styles.

However, despite its impeccable craftsmanship, the gown appeared slightly overwhelming, giving off a rigid and heavy impression. While the bold design made a powerful statement, some felt that the gown was the wrong choice and was taking away from Jada's usual grace and elegance.

Tilda Swinton (2008)

In 2008, the red carpet at the Oscars witnessed a fashion anomaly when Tilda Swinton stepped out in a dress that defied convention. The dress was, well, not the best and not very attractive. Known for her unique style, Tilda took it a bit too far with this one.

The critics said that the dress looked like a strange combination of a garbage bag and a soft, plush bag, leaving people confused. Maybe it was meant to be a bold statement that went beyond traditional fashion, but one thing was clear—it was a daring move that, unfortunately, did not quite succeed.

Faith Hill (2002)

At the 2002 Academy Awards, Faith Hill wowed us with her rendition of "Somewhere Over the Rainbow." However, her Versace gown, which featured a range of pastel hues, didn't quite hit the mark.

While singing about rainbows is one thing, wearing one on the red carpet is another. With a voice as melodious as Faith's, her enchanting performance remains memorable and a testament to her musical prowess, but even then, some fashion leaps prove a bit too high to conquer. So, she may have missed the fashion mark, but she soared high above the rainbow that night, so we might as well forgive her for this one.

Gwyneth Paltrow (2002)

Gwyneth Paltrow's choice of attire at the 2002 Oscars was definitely a head-scratcher. She opted for a gauzy tank top paired with a massive taffeta skirt, and the absence of a bra certainly caught everyone's attention.

It's safe to say that her red carpet ensemble raised more than a few eyebrows. In all honesty, the dress was not the most appealing. Even Gwyneth herself later admitted that she had some regrets. She still loved the dress, but she acknowledged that wearing a bra and opting for a simpler beachy hairstyle with less makeup would have made it work better.

Bjork (2001)

Bjork's swan dress at the 2001 Oscars was truly a unique fashion statement. Even after 22 years, this avant-garde attire still holds a special place in the history of Oscar fashion. It was definitely unconventional, which led to Bjork, unfortunately, being included in numerous worst-dressed lists at the time.

However, what's truly fascinating is that this dress went beyond the red carpet and became a cultural phenomenon, inspiring countless memes and becoming a legend in pop culture. It serves as a reminder that fashion doesn't always have to be safe; it can also be a whimsical and imaginative journey, right?

Angelina Jolie (2000)

Angelina Jolie's outfit at the 2000 Oscars, when she won the Academy Award for Best Supporting Actress for "Girl, Interrupted," was a departure from the norm. She wore a mysterious black ensemble that exuded a different kind of charm, standing out amidst the expected opulence of the event.

While not everyone was captivated by its unconventional elegance, it certainly made a statement. In a sea of vibrant colors and sparkling gowns, Angelina's choice of a lone, intriguing raven sparked conversations and left a lasting impression on the history of Oscar fashion. Her fashion journey continued to evolve, with each new chapter adding vividly to the tapestry of red-carpet tales.

Uma Thurman (2004)

In 2004, Uma Thurman made a bold statement on the Oscars red carpet. She wore a white Christian Lacroix gown that caught everyone's attention. However, the fashion world didn't quite appreciate her unique style.

The dress had frilled sleeves and an unexpected blue-and-gold waistcoat, which didn't conform to the usual red carpet standards. Looking back, Uma candidly admitted in an interview that she intentionally wanted to be on the worst-dressed lists. She felt that everyone looked the same at the Oscars that year, and she wanted to break the monotony. In her own words, "You get bored. That's when you have to say, 'I will be worst-dressed.'"

Halle Berry (2002)

At the 74th Academy Awards in 2002, Halle Berry caused quite a stir in the fashion world. While some praised her as the best-dressed actress on the red carpet, others had a different opinion.

Even the talented Elie Saab couldn't quite win everyone over with her ensemble. The combination of a mermaid skirt accentuating her hips and a sheer floral bodysuit left many questioning if she had taken a wrong turn into an underwater adventure. It's incredible how even a style icon like Halle can't always avoid a controversial outfit. It shows that even Oscar winners have their fashion missteps.

Celine Dion (1999)

Celine Dion made a bold fashion statement at the 1999 Oscars by wearing an unconventional attire that turned tradition upside down. She donned a white Dior tuxedo in reverse, creating a truly unique and daring look.

To add a touch of audacious flair, she topped it off with a rakishly tilted fedora and diamond-studded Ray-Bans. Despite being criticized for her outfit and landing on the "worst-dressed list" at the time, Celine's fashion choice has become an iconic symbol of rebellion and elegance. While other gowns may have faded away, Celine's look remains a timeless and daring addition to the diverse landscape of Oscars fashion.

Geena Davis (1992)

Geena Davis, a talent known for her remarkable performances, certainly left a lasting sartorial impression at the 1992 Academy Awards. It wasn't necessarily for all the right reasons. Her white dress was a concoction of a bustier, bubble skirt, and black spaghetti straps, and it did not quite hit the mark.

It was a bold statement of playful rebellion that still echoes in the halls of Oscar fashion history. She is known for her roles in iconic films like "Thelma and Louise" and has always been celebrated for her style, but her choice of attire that evening seems to be an exception.

Cher (1986)

By the time Cher was nominated for an Academy Award for Best Actress for her work in 1987's Moonstruck, she had already shocked the Oscars in 1986 as she unleashed her "revenge dress," setting the fashion world abuzz. The Bob Mackie gown, a black sequined creation with a daring cut-out halter and a towering feather headdress, was nothing short of iconic.

However, many labeled it a fashion failure and controversial, but Cher's bold defiance of convention made it a moment to remember. She mentioned that she chose this look because she thought the Academy did not like how she dressed.

Jennifer Hudson (2007)

In 2007, Jennifer Hudson, who won the Best Supporting Actress Academy Award, made her way down the Oscars red carpet in a look that didn't quite hit the mark. She wore the chocolate Oscar de la Renta gown, criticized by style watchers, which seemed to have found a strong supporter in Vogue editor-at-large Andre Leon Talley.

He confidently styled it with an origami-like bolero, proving that fashion is subjective and open to interpretation. Unfortunately, the ensemble didn't do justice to Jennifer's radiant talent as an actress and singer, and that's how she made it onto the list of the most poorly dressed celebrities of all time.

Anne Hathaway (2007)

In 2007, Anne Hathaway faced a fashion dilemma at the Oscars after her role in "The Devil Wears Prada." She wore a white lace dress with a large black bow that received mixed reviews from fashion critics.

Some felt the bow was too much, turning the elegant gown into a high-end prom dress. As an aspiring fashion journalist in the movie, expectations were high for Anne's red carpet look. Unfortunately, this choice turned out to be a fashion faux pas, far from the chic and polished style her character might have approved of. Even Hollywood stars can find themselves in tricky fashion situations.