The first Monday in May is synonymous with the Met Gala, a benefit for the Metropolitan Museum of Art’s Costume Institute where garments take center stage. “It isn’t about promoting a movie or playing a character—it’s all about the clothes,” says stylist Kate Young, who first experienced the event by working at it as part of her job at Vogue. “Designers live for it.” This year, the affair hasn’t happened yet—it may happen this fall—but to mark the annual occasion, Young decided to revisit some of her favorite moments from past Met Galas for the eighth episode of Hello Fashion, created with The Slowdown.

The outfits that Young loves most exemplify how the event provides an opportunity for designers and guests alike to take sartorial risks. There’s the wildly puffy, bow-covered Oscar de la Renta dress worn by entrepreneur and socialite Lauren Santo Domingo in 2012, which Young describes as “Laura Ashley on crack,” and the flower-covered gown donned by designer, stylist, and socialite Tabitha Simmons in 2014. Of Young’s clients, musician Selena Gomez’s vintage lingerie–inspired Coach dress from 2017 (one of two made for her that year) and Dakota Johnson’s 2019 fuchsia Gucci dress, which referenced a bleeding heart Madonna, top her list of greatest hits, along with a swooping 3D-printed plastic mini-dress designed by Zac Posen, in collaboration with GE Additive and the manufacturing company Protolabs, for actress and model Nina Dobrev in 2019.

The more outrageous the gown, Young suggests, the better. “The gala is home of the greatest fashion faux pas known to humankind,” she says, noting dresses with gloves attached, unflattering frocks, and the rise of the “naked dress,” which she’s still on the fence about. “I don’t know that it’s a dress if you’re completely naked with just your private bits covered by sparkles,” Young says. “But it takes a lot of courage to wear one, and I’m really impressed by the boldness of the women [who have].”

Young also details the enduring significance of the Costume Institute, an organization that was started by Broadway costume designers and dates back to 1937. “It’s one of the most important resources for designers working today,” she says. “The collection is incredible, and it’s a massive source of inspiration. The whole reason the Met Gala happens is to raise money for the Costume Institute—it’s not just a party.”

Watch new and previous episodes of Kate Young’sYouTube show Hello Fashion at youtube.com/kateyoung.