Worst Oscars Looks Of All Time (What Were They Thinking?)

Lights, camera, fashion! The Academy Awards are the grandest stage for the glitz and glamour of Hollywood, and over the years, they have given us some of the most iconic red carpet moments. But amidst all the fabulousness, let's not forget that even the A-listers are not immune to the occasional fashion faux pas. Yes, we're here to dish on the worst Oscar looks that have ever graced the red carpet. Now, don't get us wrong, the award show red carpet has given us some major fashion trends over the years. But not every fashion choice can hit the mark, especially at an event with hundreds of celebs.

The Oscars have truly seen it all, from dresses that resembled animals to outfits that seemed more fitting for an '80s prom than a prestigious awards ceremony. So, who are the guilty parties behind these awful missteps? We won't spoil all the surprises, but let's just say that even the biggest names in Hollywood have had their fair share of fashion crimes. 

From ill-fitting gowns to over-the-top embellishments, these fashion disasters have become legendary over the years, and some of them are so bad that they are somehow also good — make that make sense! Now get ready to gasp, cringe, and maybe even laugh out loud as we dissect the worst Oscar looks in all their glory.

Let's rewind to the 2015 Oscars when Lady Gaga graced the red carpet in a glittery white gown by Azzedine Alaia. It was a vision of ethereal elegance, but alas, one element ruined it all: the star's red leather gloves. Done right, gloves can be a stylish addition, but these ones seemed to have a different calling in mind. Perhaps, scrubbing the dishes or giving the floors a good polish? While the musician's style is known to be avant-garde and boundary-pushing, adding the gloves to this look took the outfit from fab to drab.

Kate Hudson's fashion choices have always had a touch of whimsy, and her 2001 Oscars appearance was no exception. She stepped onto the red carpet in a lilac dress by Stella McCartney; however, some might argue that the combination of the elaborate embellishments with the unique cape-like feature veered into costume territory. Nevertheless, it's important to consider the context, as the early 2000s were a playground for bold and eccentric fashion choices — and Kate Hudson's look certainly fit the Y2K aesthetic.

Whoopi Goldberg made a memorable fashion statement at the 1993 Oscars with her unconventional choice: not only did the Hollywood legend wear a purple and green jumpsuit, but she also decided to combine it with a purple and lime green cape. And even though the colorful jumpsuit extravaganza has since become a memorable Oscars classic, it certainly still deserves a spot on the list.

For the 2010 Oscars, Zoe Saldana decided to go with a Givenchy gown that left most fashion critics divided. There's no denying that the star looks stunning in absolutely everything; on the other hand, not even Saldana could save this dress. To put it simply, too much was happening all at once. The top was adorned with shimmering sequins, while the bottom consisted of multiple layers of tulle, each in a different shade of purple, creating an ombré effect. Separately, all of these might have looked stunning, but together, it's giving us a hot mess.

Kristen Stewart is known for her punk rock and androgynous style, which is why no one was surprised by her fashion choice at the 2022 Oscars. Sporting a black shorts suit from Chanel, she showcased her edgy persona on the red carpet. However, the combination of shorts and the glamorous event left most of us with mixed feelings, especially as there are many other punk rock ways to approach glam fashion. It was as if a punk rock rebel crashed a formal ball, which, now that we think of it, is kind of genius?

Sophia Loren, the renowned Italian actor, graced the 2009 Oscars red carpet in a yellow Armani gown that definitely wasn't everyone's cup of tea. The dress, adorned with plenty of tulle swirls, aimed to create a sense of drama and whimsy, but the execution fell short, resulting in a look that most will remember as a distraction from the star's beauty.

At the 2010 Oscars, fashionista Sarah Jessica Parker wore an outfit that some loved and others hated. As far as we are concerned, we are leaning towards the latter, as the Chanel Couture gown seemed rather uncomfortable to wear, making the "Sex and the City" star appear rather stiff.

Angelina Jolie's most head-turning fashion moment at the Academy Awards (apart from 2012 and the leg) was perhaps in 2000, when the actor wore a long-sleeved black Marc Bouwer dress. Jolie gave us major Morticia Adams vibes, and while we may not be the biggest fans of the outfit, we have to give it to her: this dark and gothic look is one of the most memorable Oscar fashion moments.

For the 1989 Academy Awards, Jodie Foster decided to go with a blue strapless bodycon dress with side detailing that definitely leaned more towards a party dress than the expected glamour of an industry event. The '80s were notorious for bold and unconventional fashion choices, and Jodie Foster's dress embodied the era's signature style, which is why we're not too mad about this one. Nonetheless, it still deserves its spot here.

Kate Winslet attended the 1996 Academy Awards in a pink gown with ample cleavage and a magenta shawl draped over her shoulders. Unfortunately, the star fell victim to an overwhelming pink palette, and the fact that the shawl appeared wrinkly gave off an unpolished appearance — something we rarely see at such a prestigious event.

Sometimes celebs wear such mismatched outfits that it truly makes us wonder whether they pick what they are wearing to the Oscars half an hour before they leave for the event. One of those looks was Jennifer Connelly's 2002 Oscars outfit. For the occasion, the actor wore a beige gown and a so-not-matching scarf that had us scratching our heads. It was like she threw everything together at the eleventh hour and hoped for the best. Spoiler alert: it didn't work.

Tyra Banks might be a fierce and fabulous supermodel, but that doesn't mean she is a stranger to fashion fails. At the 2000 Oscars, the model wore a gown that veered into costume territory, giving us major princess energy. The silk corset paired with the fluffy tulle bottom created a clash of styles and fabrics that made us wonder whether Banks was attending the Oscars or auditioning for a Disney musical.

Decked out in an Alexander McQueen gown, Gwyneth Paltrow went for a sheer gray/beige bodice paired with a voluminous black maxi skirt for the Academy Awards in 2002. The result? A gothic vibe that may appeal to the Y2K fashion enthusiasts right now, but was certainly not well received back then. Gwyneth's Alexander McQueen creation is undoubtedly cool and edgy, but not Oscar red-carpet worthy.

In 2007, Jennifer Hudson wore a stunning brown Oscar de la Renta dress that gave us all elegance and sophistication we needed. This could have been a look for a "best dressed" list, but unfortunately, the fashion gods had other plans in store. Enter the metallic bolero, stealing the spotlight and leaving us wondering why it had to crash the party.

Hold on tight as we journey back to the 1986 Oscars and witness a moment that still leaves us dazzled and perplexed, even almost 40 years later. Now, we have to tread carefully here, as criticizing the iconic Cher's style is almost sacrilege. However, this ensemble simply missed the mark. The star opted for a feathered headdress that would make even the most glamorous showgirl envious. Designed by the renowned Bob Mackie, it looked like it would have worked better on a dazzling Vegas stage than the most famous red carpet in Hollywood.

Television personality Kelly Ripa is usually known for her chic and polished style, but her 2018 Oscars outfit was everything but that. The star wore a black gown that seemed simple and elegant from the front, but its green and pink hues collided in the back. Designed by the talented Christian Siriano, this gown attempted to redefine the concept of business in the front and party in the back, but if you ask us, this was a risk not worth taking.

Geena Davis's 1992 Oscars look was a collision of '80s prom glamour and '90s goth vibes, neither of which really fit an Oscars red carpet. Now before you come at us, there are classy ways one can incorporate either of the two into an Academy Awards outfit, but Davis failed to do that. The star stepped onto the red carpet in a white high-low dress adorned with ruffles and swirls, paired with white gloves, black straps, and black tights and heels (adding a touch of '90s goth mystique to the mix).

Musician St. Vincent is known for her unconventional charm, which often translates to the red carpet. To the 2018 Oscars, the star wore a fun outfit from Saint Laurent featuring a single, voluminous pouf sleeve and a mini dress that was so short it seemed as if the lower half of her outfit just went on an impromptu vacation. Now, we admire her boldness and the audacity to challenge traditional fashion norms — but wearing something like this to the Oscars seemed like a deliberate bid to steal the spotlight and command all eyes on her.

In 2019, Linda Cardellini graced the Oscars red carpet in a hot pink explosion that left jaws dropping — and most of them not for a good reason. The star wore a fluffy Schiaparelli Couture dress, drenched in a vibrant shade of pink, with a baby pink satin bow cinching the waist. Now, Cardellini has never been one to shy away from making a statement with her fashion choices. However, as we explore the world of Worst Oscars Looks, we can't help but question the excessive fluffiness of it all.

At the 2023 Oscars, Ana de Armas was draped in a silver Louis Vuitton gown that had all the makings of a show-stopping ensemble, but nevertheless fell short. The mermaid shape of the gown was undeniably striking, exuding a sense of elegance and glamour. The intricate design and impeccable tailoring showcased the label's signature craftsmanship. However, the light silver color washed her out, leaving her looking somewhat pale and lacking the radiant glow we've come to associate with her. Indeed, color is a powerful tool that can make or break a look.

In 2002, Naomi Watts stepped onto the Oscars red carpet wearing a black Gucci dress that left us utterly uninspired. The gown, while elegant, was simply too safe and predictable for such a grand occasion. We expect drama, and we crave glamour — and unfortunately, this look fell short on both fronts.

In 1990, Kim Basinger graced the Oscars red carpet in a white ball gown skirt with one glove, half a blazer, and a whole lot of confusion. The pieces seemed mismatched — it was as if she took a fashion jigsaw puzzle and put it together all wrong.

Nicole Kidman made a daring fashion choice at the Oscars in 1996 when she stepped onto the red carpet wearing a purple Dior nightgown. While simplicity can sometimes be elegant, this particular gown seemed to veer into sleepwear territory — and it left much to be desired.

Salma Hayek's Gucci lavender gown at the Oscars in 2018 had the potential to be a stunning red carpet moment, but it quickly became a case of too much of a good thing. The all-over sequins and blinged-out neckline were glamorous, but they ended up overwhelming the overall look.

We couldn't help but feel a pang of sympathy when we saw Maya Rudolph in her red Valentino gown at the 2018 Academy Awards. The turtleneck style may have seemed like a good idea, but it ended up swallowing the actor whole. The vibrant red color was meant to make a statement, but it was the overwhelming amount of fabric that stole the show. The voluminous silhouette and high neckline completely enveloped the star's frame, which is certainly a shame.