If the fashion world had a vote, they’d surely nominate Halloween as the most wonderful time of the year. The runway evidence is compelling: Thierry Mugler’s fantastical insect creatures for spring 1997, Alexander McQueen’s Salem-inspired collection for fall 2007, Miuccia Prada’s Frankenstein prints for fall 2019. Clearly, some designers have trouble waiting until October. So when the occasion finally arrives, you can imagine the wardrobe deliberations.

And then there’s the question of where to wear it. “In the ’90s, Naomi and Kate would have amazing Halloween parties,” recalls Anna Sui, who revisits her costume inspired by The Bride with White Hair and shares with us a snapshot of the look taken by none other than Sofia Coppola. More recently, Allison Sarofim and Stuart Parr’s legendary fêtes had guests interpreting themes as ambitious as Italian Futurism. And now, Ivy Getty’s Halloween parties are keeping the tradition going. These are invitations that require a little homework.

Ahead of the holiday, we asked fashion designers and friends to revisit their best looks. Many favorites turned out to predate their fashion careers: Juju Vera’s Juju Ferentinos’s childhood snowy owl was hand-sewn by her mother with silk, feathers, and rhinestones. “This was essentially a haute couture owl,” she remembers. A pint-size Carolina Herrera’s Wes Gordon, meanwhile, delighted in trick-or-treating as a “very scary leopard.”

Others found their finest disguises a little later. Tanner Fletcher’s Tanner Richie and Fletcher Kasell dressed as Mary-Kate and Ashley Olsen in thrifted clothes, “finished with sunglasses from The Row.” Lynn Yaeger’s entirely vintage 1920s flapper ensemble, meanwhile, proved almost too convincing: “Many people didn’t even realize I was in costume…”

Their favorites—and the photographic evidence—below.

Anna Sui as The Bride with White Hair

Photo: Courtesy of Anna Sui