I'm not sure which of my embarrassing traits to blame for my enduring obsession with Halloween: my early exposure to, and subsequent love of Tim Burton movies, the fact that I am a Scorpio, or my not-so-secret past as a theater kid. Growing up, the rest of the year was simply a lead-up to the main event. I would spend hours pouring over face paint tutorial books, browsing thrift stores with my mom, and mapping out the best trick-or-treat route (a house on Walnut Street had a cotton candy machine going every year). For a seven-year-old whose fashion idols were Cruella De Vil and Carol Burnett's Miss Hannigan, Halloween represented an invitation to indulge in a sugar high and live a fantasy for a night—which was and remains to be a bitter, yet stylish, spinster.
Halloween can be a polarizing holiday, but those who love it love it. "Wearing something you wouldn't normally wear sort of resets you," jewelry designer Scosha Woolridge comments. "It shakes up the repetitive patterns, which is so fun and can be totally freeing." Even if costumes aren't your thing, Halloween can be an excuse to gather friends for apple cider and toasted pumpkin seeds, marvel at strangers' spooky sartorial genius, or wander around your neighborhood and enjoy the decorations (unless you're Joyce Carol Oates). Below, a few friends of Coveteur recall favorite Halloween costumes, memories, and traditions to get you in the spirit.
Photo: Courtesy of Mónica Santos Gil
“It's hard to pick just one favorite Halloween costume, but the most special ones have definitely all been on the DIY side. When I was young, my mom would spend weeks hand-making costumes for me and my sister, something which I adopted as I grew older and learned how to sew. It has since become a Halloween tradition I look forward to. I'll either sew something from scratch or alter existing pieces in my wardrobe that could work for the specific costume I have in mind. I'll usually also hand-make accessories to go with it (a bag or jewelry piece) and pair it with elaborate makeup."
“I was invited to a Halloween party many years ago and was scrambling to find a costume! At the last minute, I made it myself. I decided to go as a SEXT and hand-painted a sultry text exchange on an old t-shirt. I wish I still had that shirt—could have been a great day-to-day piece! My favorite Halloween tradition is going to the drugstore the day after for half-priced candy!”
Photo: Courtesy Julia Cumming
“My favorite Halloween costume I've ever done is Sexy Bernie Sanders. I can't remember why I thought of this…I think it was a case where I thought it would be hilarious and then I just couldn't stop myself from doing it. Plus, my best friend Alya agreed to be AOC, so it was just too perfect. My hairstylist Chelsey Pickthorn helped me slick my hair back and tease out the sides to create this really exaggerated wild look. I think we've all been inspired by Bernie's windswept and carefree event hair at some point. I remember that it wasn't until very late in the evening that I realized it might not actually be a sexy costume and that I may have shot myself in the foot as far as some Halloween romance. But I didn't mind. I was DJing and I danced all night long, which is a perfect Halloween in my eyes. And then a few months later, I actually got to meet Bernie when I performed at a couple of his campaign events in New Hampshire! It was some fun foreshadowing. Those shows ended up being major highlights in my life.”
Photo: Courtesy of Michelle Duncan
“Favorite Halloween look: Wednesday Addams! The inspo for the look was The Addams Family for a Halloween party in 2019. I wore one of my dresses from Duncan and had my friend Noor as my Wednesday Addams twin. This particular costume stands out for me as I wore Duncan with goth girl makeup, went to the party, and straight to the airport for a flight to London in the costume and makeup! My favorite tradition for Halloween is listening to 'Monster Mash' and planning the look every year!"
“My all-time favorite Halloween costume is when my old coworkers and I (from Teen Vogue and Allure) dressed up as different versions of Solange. I am a huge fan of Solange's music and her boundary-pushing sense of style, so paying tribute to her was a no-brainer. It was probably my most ambitious costume undertaking as I had to source many of the outfits, including the purple yarn from the 'Cranes In The Sky' video that we literally wrapped around Jihan Forbes, and the Schutz gladiator sandals Solange wore to Fashion Week that I found for Hanna Howard to wear.
“I knew I wanted to wear the cape dress and Afro look from her wedding, so that was probably the easiest costume to pull together. A fun fact is that our market editor at the time, Brian Giuducci, called in the exact Erickson Beamon dress Solange wore to SNL, so we were pretty excited about that. We didn't have a costume competition at Condé Nast then but if we did, we certainly would have won it—hands down!"
Photo: Courtesy of Rachel Rabbit White
“My favorite Halloween costume was when I went as Cicciolina, the Italian porn-star-turned-senator who was briefly married to the artist Jeff Koons and inspired his Made in Heaven series. The work (photos, sculptures) blurred the lines of pornography and art, of good taste and bad, but I Iove how it felt like the relationship itself was the true work of art.
“Every year I go to this party called Spooky Snacks in New York hosted by a couple friends of mine, one half of which actually used to work for Jeff Koons. It was the perfect party to be Cicciolina because people there actually knew who I was! My friend who worked for Koons even pulled out a prized possession he'd found in the trash while working there—an airbrushed tee shirt (the kind you get in trashy beach towns) that said ‘Jeff Loves Cicciolina.’ You know, with palm trees and hearts. Somehow it all felt perfect for Halloween; I mean, what's more terrifying than romantic love?”
Photo: Courtesy of Natasha Stagg
“When we were in fifth grade, our mom thought it would be funny if my twin sister and I went as a hippie (her) and a punk (me). Neither of us really understood what those terms meant, then. This is us on our way to school. I think Halloween parties are usually not as fun as just wandering around, seeing everyone on their way to parties, in costume or not. The same goes for New Year's Eve.”
Photo: Courtesy of Vita Haas and Lucy Weisner
Photo: Courtesy of Vita Haas and Lucy Weisner
Photo: Courtesy of Vita Haas and Lucy Weisner
“Each year Vita and I (Lucy) try to plan a Halloween costume together. For the past few years, we've done Romy and Michelle, Mary Kate and Ashley in the movie New York Minute, and also an angel and devil. We've always liked dressing up together especially as characters that we relate to and where there's some overlap between us and them—like Romy and Michelle who open a store at the end of the film.”
Photo: Courtesy of Haile Lidow
“Keeping track of more than 5,000 pieces of clothing and accessories could make anyone crazy. Add in a global pandemic and making a short film, it's safe to say that being a 'Basket Case' may be more than just my Halloween costume this year! My fruity state of mind and this newly-restored Bill Cunningham headpiece led me to get naked in my garden and throw on a cornucopia of fruity accessories.
“My girlfriend calls October ‘spooky season,’ and over the years she's basically forced me into loving scary movies. I play dress-up all year round, so my favorite part of Halloween is always the candy.”
Photos: Courtesy of Dana Donnelly
“Picture this, it's October 2017. Rumors are circulating that Kylie is pregnant with her first child but it's unconfirmed. Many, myself included, are positive that she is pregnant based on the fact that the Instagram content she's posting features her wearing no form-fitting clothing. At this point, I'm a huge Kylie stan. I would have died for her in 2017!! I decide to recreate an oversized shirt look by typing the following key terms into Amazon: 'blue striped collared shirt' and 'blonde ombre wig.' I get my nails done to match hers. Boom, done! Brilliant costume that will forever stand out in my memory because of the deep cultural significance (Kylie's FIRST secret pregnancy). At the Halloween party I went to that year, I ran into OTHER people who were also perpetuating the Kylie pregnancy rumors with their costumes. My twin (quadruplet?) flames!
“Halloween traditions I look forward to every year include taking a hot picture in my costume and raking in those IG likes, baby!”
Photo: Courtesy of Scosha Woolridge
“Growing up in Australia, where Halloween doesn't get anywhere near the attention that it does here in the States, my family didn't get too involved other than to give a dry Weet-Bix to the odd trick-or-treater that rang our doorbell. Yum... not! I moved to America in 2003, and that was the first time I witnessed the costume craze—it totally blew my mind. Only since having kids 10 years ago did I begin to really think about costumes and how to really celebrate the holiday.
“Being a designer, I prefer to create my own look from whatever I envision, but I also rarely can find the time between running a business and my family. So for me, it always ends up being a last-minute, thrown-together mish-mash of whatever I can find—and at that point, I never really know what character I'm meant to be. A few Halloweens ago, I found this hot pink bob and red bodysuit at a vintage store, so I popped into Party City to see if I could find some eye glitter... and voila! My outfit was something like Jetsons-meets-anime. Whatever kooky character I was (or wasn't), I felt good, I felt hot. A tight bodysuit with a zipper will do that, you know? I think that wearing something you wouldn't normally wear sort of resets you. It shakes up the repetitive patterns, which is so fun and can be totally freeing.
“My family doesn't really have any special rituals around Halloween. We'll make a lantern or two. It's mostly for the kids, and all they care about is the bags of sugar they're about to devour!”
Photo: Courtesy of Isabella Lalonde
“My favorite Halloween costume is a rendition of a berry fairy,' which is a made-up character I consistently use within my fantasy art. I used colored eye contacts and my own jewelry products to enhance the surrealism of the character. Personally, I love making collages with my self-portraits so I chose to use a strawberry skin background and turn my skin green. For new Halloween traditions, I'm super excited that this year I will be hosting a pop-up with my favorite thrifter, Emma Rogue. Beepy Bella (my brand) and Rogue Arms will be having a Halloween spooky circus pop-up on October 30th featuring a limited edition baby tee collaboration and tons of eclectic vintage finds."
Photo: Courtesy of Instagram/@dressupwithjess
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