As it plays host to Hollywood A-listers from all over the world, the Annual Academy Museum Gala should be one of the year’s greatest fashion events.
But, as they arrived at the star-studded 5th annual Gala at the Ted Mann Theatre in LA on Saturday night, several stars failed to impress, despite a series of bold and striking looks.
Among the style blunders was a peculiar masked look from none other than red carpet queen Kim Kardashian – which left her head entirely covered by a flesh-toned mask.
The SKIMS founder, 44, donned a tan-colored gown with a corset bodice that flaunted her toned figure in a move that left many wondering if she was celebrating Halloween early.
The mask encased her entire head and hair as she posed for photographers in a nude Maison Margiela gown with a skintight corset bodice.
The gown also had sleeves attached to the hem of the skirt, creating a bat-like wing effect as Kardashian raised her arms to fix her mask or place her hands – which displayed a claw-like manicure – on her waist.
American actress Elle Fanning, 27, also suffered from a rare fashion miss as she opted for a Balenciaga ensemble with a bizarre red feathered skirt.
The look seemed to be even more unusual as she turned to the side, as the red embellishment was only attached to the front of the look.
Among the style blunders at the Annual Academy Museum Gala was a peculiar masked look from none other than red carpet queen Kim Kardashian
American actress Elle Fanning, 27, also suffered from a rare fashion miss as she opted for a Balenciaga ensemble with a bizarre red feathered skirt
Also opting for feathers was actress Naomi Watts, 57, who showed off her sense of style in a light blue dress and simple black heels.
Despite the stunning flow of the dress, aspects such as the opened-up shoulders and the sudden addition of the feathers at the end took away from its simple effect.
Cara Delevingne, also 33, dazzled in a glitzy silver gown with a ruffled blue neckline.
The halter neck design ensured Cara turned heads throughout the evening, while gorgeous floral details connected the dress at the back.
However, the blue ruffles sat awkwardly on her neck, accidentally becoming the statement piece of the ensemble.
The White Lotus star Michelle Monaghan appeared to have been inspired by giant floral floats as she paraded down the red carpet in a very voluminous Carolina Herrera number.
The 49-year-old’s purple ensemble was straight from the designer’s Spring/Summer 2026 ready-to-wear catwalk, but it overwhelmed her completely.
The huge dress featured an empire waistline with large puffed sleeves and a full skirt, covered with 3D flowers and a black ribbon in the centre of the waist.
Michelle Monaghan attends the 5th Annual Academy Museum Gala at the Academy Museum of Motion Pictures, Ted Mann Theater
Elsewhere model Cara, 33, dazzled in a glitzy silver gown with a ruffled blue neckline as she posed
The back featured beautiful flower detailing – however a blue ruffle detail sat awkwardly on her neck
Actress Naomi Watts showed off her sophisticated sense of style in light blue feathered dress and simple black heels
Naomi made an appearance with her husband Billy Crudup
Michelle’s make-up and hair also drew some raised eyebrows from fans. Her hair was pulled back into a low bun with a middle parting, with no layers or strands to frame her face, and her dark eyebrows and dark red lipstick were in stark contrast to her pale skin.
Da’Vine Joy Randolph usually delivers high glamour and elegance on the red carpet, but missed the mark at this year’s Academy Museum Gala.
The actress, who was named one of Time magazine’s 100 most influential people in the world in 2024, opted for an all-white ensemble.
The strapless dress featured a floor-length skirt that appeared to be an awkward length, crumpling on the floor at her feet.
But the most strange feature of the dress was a voluminous tulle ruffle that circled her waist and hips, which appeared almost frumpy in design.
Wednesday star Jenna Ortega is known for choosing bold, often goth-inspired outfits when she attends big events. But while her look at the gala was no less bold than usual, it was a rather disappointing ensemble.
Wearing a runway look from Grace Ling’s Spring/Summer 2026 collection, Jenna’s torso was covered by a sculpted metal plate that followed the contours of her figure, leaving her back almost completely bare.
However, the daring top was in stark contrast to the shiny brown column skirt, which was rather boring in comparison – as was her hairstyle, which was swept into an updo with strands of her fringe covering one of her eyes.
Zoe Kravitz hid her fantastic figure in so many ruffles and puffed fabrics that she was totally overwhelmed by her dress
Jenna’s torso was covered by a sculpted metal plate that followed the contours of her figure, leaving her back almost completely bare
Her skirt was almost boring in comparison to her striking top
Zoe Kravitz hid her fantastic figure in so many ruffles and puffed fabrics that she was totally overwhelmed by her dress.
The actress, who is rumoured to be dating Harry Styles, chose a dramatic dress by Saint Laurent that featured layers of ruffles all across the bodice of the dress as well as the skirt, and well as huge puff sleeves that completely covered her arms.
The backless dress showed off her tattoos and toned back. She wore her hair very short in a pixie cut with micro bangs framing her face, and wore minimal accessories, opting for just a ring on her right hand.
On the runway, Kristen Wiig’s Chanel outfit appeared polished yet loose and sexy – but the comedian did not do the flowing gown justice on the red carpet.
Kristen’s outfit comprised of a white polo neck-style top with long, loose sleeves that she rolled up to expose her forearms, paired with a bold red tiered rah-rah skirt with a white waist panel and a belt.
The expressive skirt had an asymmetric hemline that revealed Kristen’s black pumps that matched her black belt, with a train that trailed behind the 52-year-old star.
Kristen accessorised with chunky red-and-white necklaces to complement the colours of the skirt and a chunky bracelet, with her shoulder-length hair slicked down.
However, without the train, Kirsten’s look appeared to be more office appropriate than red carpet.
Actress and director Rebecca Hall wowed in a paint-effect corset dress
She looked great in the quirky number – but the daring top of the look seemed at odds to her very formal black maxi skirt
On the runway, Kristen Wiig’s Chanel outfit appeared polished yet loose and sexy – but the comedian did not do the flowing gown justice on the red carpet
A sheer dress can often be a bold and sultry look for a red carpet, but Mikey Madison’s Dior choice appeared to be a fashion misstep
A sheer dress can often be a bold and sultry look for a red carpet, but Mikey Madison’s Dior choice appeared to be a fashion misstep.
The grey full-length lace gown featured embroidery details, cinched puff sleeves and a ruffle hemline on the skirt, as well as an awkwardly tied thin grey-silver ribbon.
Charli XCX led the famous faces posing up a storm as she rocked a dramatic black lace and leather gown with a daring neckline and drop waist.
The newly married singer, 33, was sure to turn heads in the structured number which was accessorised with a diamond necklace.
However, her thick black leather skirt gave a heavy feel to the entire outfit, and overwhelmed its overall impression.
Another of the more quirky looks included actress and director Rebecca Hall, 43, who opted for a bold paint-effect corset dress.
The look left little to the imagination, though the lower half of the look was much more formal, with a simple black maxi skirt.
Olivia Wilde looked sleek in a black Saint Laurent maxi dress as she attended the gala.
A sea of stylish British celebrities were out in force for the star-studded 5th Annual Academy Museum Gala in LA on Saturday night, including Charli XCX
She looked great in the black leather dress which featured a lace trim on the cleavage – however the skirt appeared to overwhelm the ensemble
Da’Vine Joy Randolph usually delivers high glamour and elegance on the red carpet, but missed the mark at this year’s Academy Museum Gala
Adding chunky jewellery and glamorous make-up, the relatively simple dress allowed the director to glow.
But with such a stunning range of bright and bold ensembles, Olivia’s monochrome look swayed slightly on the dull side and appeared not quite fitting for the red carpet.
Other British stars in attendance included Ed Sheeran, Jude Law, Eddie Redmayne and Orlando Bloom.
This year’s gala co-chairs included celebrities such as Jon M. Chu, Viola Davis, Robert Downey Jr. and Jennifer Hudson.
Amy Homma – the Academy Museum director and president – recently issued a statement in regards to Saturday’s ceremony, per The Hollywood Reporter.
‘The Academy Museum gala is a special evening dedicated to bringing together individuals to champion the celebration, advancement and preservation of cinema.’
Homma added: ‘As we gather for a fifth year, we are honoured to recognize Penelope Cruz, Walter Salles, Bruce Springsteen and Bowen Yang – storytellers whose influence has been proven to resonate in film and beyond.
‘We are so thankful to founding supporters of the museum, including our partner Rolex, for their long-standing commitment to cinema, and our co-chairs for hosting this important event.’
The event raises money for the museum, including for their exhibitions and education programmes.
