Within the realm of the Met Gala, there exists a dichotomy between those who embrace worldly beauty and those who adhere to the adage “Beauty is pain.” Over the years, Anna Wintour’s annual extravaganza, held every first Monday of May, has transcended from a mere gathering of luminaries to a spectacle of unparalleled stylistic audacity. Reflecting on the event’s history, one cannot overlook the iconic moments, such as Lady Gaga’s triumphant 2019 metamorphosis, seamlessly transitioning through three distinct ensembles, or the feline allure of Doja Cat’s presence last year. It’s a platform where celebrities willingly embrace radical and sometimes perilous measures to craft jaw-dropping looks. Let’s delve into the realm of the most memorable and daring transformations showcased at the Met Gala.

Renowned for their omnipresence in the realm of celebrity gossip, the Kardashian-Jenner family has long been fixtures at the Met Gala. Each of Kris Jenner’s daughters has left an indelible mark with their striking ensembles. Notably, Kim Kardashian’s penultimate appearance at the Gala saw her undergo drastic weight loss to don a vintage dress worn by Marilyn Monroe during her iconic “Happy Birthday” serenade to President John F. Kennedy in 1962. In 2019, she captivated in a Mugler creation inspired by Sophia Loren’s damp attire in “Boy on a Dolphin,” sacrificing comfort for style with a form-fitting dress and tight corset that rendered sitting impossible. Kendall Jenner made headlines in 2022 when she resorted to unconventional measures, documented on their reality series, by urinating in a bucket en route to the Met Museum. Meanwhile, Kourtney Kardashian faced a fashion crisis the same year, requiring the expertise of Thom Browne’s tailoring team to sew her into her skirt. These instances underscore the lengths to which stars go for the sake of fashion at the Met Gala.

Zendaya’s Met Gala experience in 2018 transformed into a physical challenge as she embraced the Heavenly Bodies theme alongside Versace, crafting an armor reminiscent of Saint Joan of Arc. Composed of intricate silver chains, the attire was not only visually striking but also physically demanding, requiring her to ascend the Met stairs despite its weight, all while balancing in heels. Similarly, in 2021, Simone Biles donned a breathtaking 40-kilogram dress by Area, a shimmering silver structure adorned with crystals, embodying both grace and strength. Amidst these remarkable transformations, some efforts may seem minor, like Harry Styles piercing his earlobe to complement a Gucci earring in 2019—an ode to the enduring adage that “beauty is pain,” where discomfort becomes a testament to dedication.