Luke Meagher, the founder of the popular social-media handle HautLeMode, has been lauded for bringing “fashion criticism to the digital age.” With nearly 380,000 followers on Instagram and a YouTube channel with 850,000 subscribers, the content creator (who recently signed with UTA) breaks down everything from the latest runway shows to the biggest Hollywood red carpets. Recently for THR, he sat down opposite Jenna Lyons to give his take on the 2024 Oscars.

Now, Meagher is sharing his highly opinionated views on which Met Gala dresses ranks as the best and worst of all time, ahead of fashion’s biggest night taking place at the Metropolitan Museum of Art this coming Monday, May 6.

Rihanna in Guo Pei (BEST)

Meagher names his favorite Met Gala look of all time as Rihanna’s appearance in 2015. “Rihanna’s wearing of the golden Guo Pei shawl cape with such an extravagant train length will go down as the best moment the Met Gala red carpet has ever seen. Not only was the look immortalized in the documentary The First Monday in May, and still gives me chills when I think about the montage of her ascending the stairs to the melodic voice of Frank Sinatra, but it was also a true coinciding of fashion and popular culture,” he says.

Meagher adds that, “The fact that this beautifully embroidered and fur lined cape by a Chinese haute couturier can be both one of the most beautiful examples of Chinese craft and clothing design, while being meme’d as Rihanna wearing a gigantic breakfast omelet was the perfect meeting of both the fashion world and the wider world where they are. The fashion world can provide beauty and stunning garments for the planet to ‘ooh and ah’ about, while the rest of the world can always find a witty jab to bring everyone back down to earth.”

Jackie Kennedy (BEST)

For the 1979 gala, showcasing the exhibit Fashions of the Hapsburg Era: Austria-Hungry, Jackie Kennedy “stunned in a strapless black organza Valentino gown with flounces and frills that perfectly showcased Valentino Garavani’s voluminous works.”

Sarah Jessica Parker (BEST)

Sarah Jessica Parker’s dress in 2022 by Christopher John Rogers — which was an ode to designer Elizabeth Keckler, who had been the dressmaker to Mary Todd Lincoln — “showed her dedication to fashion history [and] glamour in such a wonderful way,” says Meagher. “She is consistently one of the most enthusiastic Met Gala attendees.”

“Her choice of designer Christopher John Rogers, known for his voluminous gowns and graphic motifs perfectly mixed with the theme of Gilded Glamour from that year, that required an understanding of late 19th century dress,” continues Meagher.

Claire Danes (BEST)

Claire Danes light-up Cinderella dress is a defining look of the Met Gala red carpet, as it was one of the earliest points that technological and electric advancements were on full display on the Met steps,” says Meagher. “Posen’s sculptural gowns are always a feat, as the ability to drape such forms seems to be falling away from modern fashion, but to combine it with fiber-optic technology that when the lights are dimmed shone a beautiful blue hue only further enhanced the theme of the year about fashion and technology.”

Zendaya (BEST)

“Zendaya is another Met Gala attendee who truly lends herself to theme dressing, but her most memorable has to be a Joan of Arc-inspired Atelier Versace chainmail gown worn to the [2018] Heavenly Bodies exhibit,” says Meagher. “While most wore crosses or nods to Catholic symbolism, Zendaya channeled the Patron Saint of France, Joan of Arc, whose wearing of men’s clothing got her executed in 15th-century France. Zendaya transformed the battle-ready chainmail into a cold shoulder classic with grace and wit, channeling the medium and attitude of her inspiration Joan of Arc during her heresy trials.”

Cher (BEST)

“Cher’s iconic silver fringe and nude illusion gown by Bob Mackie worn to the 1974 gala was not only drop-dead gorgeous, but has also become a fashion moment that inspires to this day,” says Meagher.

“Before the advent of Hollywood stylists and fashion designers clamoring to dress celebrities, it was Hollywood’s costume designers who often made the wardrobes of famous celebrities and actors,” he adds. “And seeing how it was designed by her collaborator and friend Bob Mackie, and went on to garner a Time Magazine cover as well as a huge amount of publicity for the Met, it is a perfect example of fashion kismet.

Kim Kardashian (WORST)

In 2022, says Meagher, “Kim Kardashian’s wearing of the famous 1962 Jean Louis-designed and Bob Mackie-sketched gown for Marilyn Monroe was a travesty. A piece of American history was ruined that day, as there is no way the dress fit properly, and both seen and unseen damage was caused to the dress due to the wear. Rhinestones missing, weaves stretched, and sweat and makeup will have all left permanent marks on that dress that was made specifically for Marilyn. While many thought it not that big of a deal, I wonder if they would think the same of Kardashian painting over a Jackson Pollock or Georgia O’Keefe?” Kardashian and the dress’ owner, Ripley’s, both deny reports it was damaged.

Kylie Jenner (WORST)

“While Kylie Jenner’s ode to the late Virgil Abloh was a nice gesture,” says Meagher, “her gown over a sheer T-shirt with the veiled baseball hat didn’t fit the [2022] theme of Gilded Glamour. It didn’t feel particularly fashion forward.”

Madonna (WORST)

“With [2017’s] avant-garde dress code theme, some might think Madonna’s ‘Combat Barbie’ camouflage
gown by Moschino was right on the money,” says Meagher. “But it leaned more tacky, rather than ahead of its time like it was supposed to. Many celebrities embodied the exciting and transgressive notion of honored designer Rei Kawakubo, who was the theme of that year, without making their looks feel like costume party couture.”

Jared Leto (WORST)

“While having fun with your Met Gala outfit is usually the most important goal for attendees, turning your attire into an actual costume is where it goes a bit too far,” he says of Leto’s 2023 cat suit representing Karl Lagerfeld’s cat, Choupette. “It lost the aspect of fashion design — unlike Doja Cat who appeared as Choupette as well — and just felt like something rented from a costume shop.”

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A version of this story first appeared in the April 24 issue of The Hollywood Reporter magazine. Click here to subscribe.