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
“In the ’90s, Naomi and Kate would have amazing Halloween parties. Sofia Coppola took this photo of me. Hong Kong was having a New Wave of directors turning out incredible films. My costume was based on The Bride with White Hair, starring Leslie Cheung and Brigitte Lin.” - Anna Suit
Jordan Roth as RIP Barneys
“My favorite is my most recent from last Halloween. I was judging the costume contest at Bette Midler’s Hulaween and the theme of the evening was New York, New York, a Helluva Town!…so I went as RIP Barneys! An homage to one of my favorite fashion haunts and to legendary Simon Doonan and his extraordinary window displays. Machine Dazzle created this magic for me.”
Vera Wang as Cher
“As a Halloween devotee, I was determined to commemorate the holiday despite the pandemic! This is my ultimate Cher tribute… someone I have always admired for her talent, creativity, and courage!”
Wes Gordon as a leopard
“Presenting Wes, the leopard. He was two or three in the photo and loved trick-or-treating as a ‘very scary leopard.’”
Batsheva Hay as Mia Farrow in Rosemary’s Baby
“My favorite, in 2023, was a spin on Rosemary’s Baby, where I walked around in front of the Dakota with a pram that had smoke coming out of it. I was basically a prairie version of Mia Farrow with a demonic baby. We kept the pram for the day, and it was incredibly fun.”
Juju Ferentino as Snowy Owl
“Me as a snowy owl, c. 1999. Apparently, I had an obsession with Arctic animals when I was little. Snowy owls, snow leopards, polar bears, etc. Don’t ask me why! My mom took my costume ideas very seriously. This was essentially a haute couture owl; she sewed it entirely by hand with silk, feathers, and rhinestones. Completely over the top. Looking back, I think I inherited much of my imagination from her.”
Tanner Richie and Fletcher Kassel as Mary-Kate and Ashley Olsen, 2021
“We went as Mary-Kate and Ashley Olsen in 2021. We don’t often dress up for Halloween, but from one duo to another, this remains a favorite. The looks were thrifted, finished with sunglasses from The Row.”
Lynn Yaeger as a 1920s Flapper
“I spent hours curating this authentic 100% vintage 1920s flapper costume—even the shoes!—but when I got to the Lanvin Halloween party at their store on Madison Avenue, I realized it didn't look that different from my normal clothes! Many people didn't even realize I was in costume...”
Fernando Garcia as a Ninja Turtle
“Donatello, for whatever reason, was always the one with the strongest soul… plus the best weapon.”
Contessa Mills as Veruca Salt from Charlie and the Chocolate Factory
“This is Veruca Salt in blueberry form, and once she is juiced. I enjoy looking funny but also sexy, so this allowed me to do both, which is why it is my favorite. It also felt silly to dress up the inflatable suit with a neck bow, full makeup, and Louboutins.”
Gigi Burris as a beekeeper
“My favorite costume: About five years ago, my husband and I dressed as beekeepers, and each bee was crafted by hand from chenille and tulle. The bees were placed onto French netting, and my honey pot was crafted from a sewn Milanese braided straw. The entire spirit feels like a recent Thom Browne show!”
Elena Velez as a pumpkin
“My brand is one long series of esoteric and self-serious Halloween pageants, so here’s a memento from a lighter time under a different creative director (my mom).”
Presley Oldham as a cowboy
“I wear the same cowboy Halloween costume every year—vintage fringe chaps and matching vest, with an undershirt and tights I made out of a vintage desert-scape tablecloth. It’s a classic and easy to wear but very effective. My partner Tyler, seen here as a sleepy guy, loves Halloween and always switches up his costume. So his date each year is always a cowboy, even if he’s a pirate or sailor.”