November 1, 2019 6 min read

In 17th-century France, kings dressed for the day in front of a live audience. 

On Thursday, the queen of Halloween did the same — but instead of donning regalia, she opted for a gory alien costume that took more than 12 hours to get into. The live audience, in her case, was New York passersby with smartphones pressed to the glass windows of midtown’s Amazon Bookstore. 

Supermodel Heidi Klum’s over-the-top costumes and Oct. 31 blowout bash have been making headlines for 20 years. Some of her most legendary getups: Fiona from Shrek (2018), Teen Wolf (2017), Jessica Rabbit (2015), an old woman (2013) and an ape (2011). This year, Klum’s husband Tom Kaulitz complimented her costume by dressing as a bloody astronaut after an alien attack. 

This was Entrepreneur ‘s first time covering the event, and one thing is clear: Heidi Klum knows creative, long-term growth. The multimillionaire leveraged her modeling career into a business venture through hosting and production roles on shows like Project Runway, America’s Got Talent and Germany’s Next Top Model, and she’s launched multiple clothing lines, including a line of shapewear, swimsuits and lingerie. She’s applied the same boldness and attention to detail to her annual Halloween extravaganza, which has blossomed into a veritable institution in the public eye. 

As someone who loves dressing up (I was a college theatre kid) but also tends to procrastinate on online ordering, my Halloween costumes usually end up somewhere in the neighborhood of could’ve-been-great-if-I’d-planned-further-ahead-of-time. This year, with an invite to #HeidiKlumHalloween in hand, I wasn’t going to let that happen. Two-day shipping was my best friend, as was the fact that Entrepreneur’s office is in Herald Square, which allowed me to stop by Target, Macy’s, Duane Reade and Abracadabra costume store on my lunch break or right after work. A friend and I opted to dress as escaped aliens from Area 51, complete with extended alien eyes on headbands, silvery wigs, iridescent green outfits and purple skin (thanks to covering our entire faces in Urban Decay eyeshadow). 

We arrived earlier than most guests to check out the red carpet and get the lay of the land. This year, Klum hosted her party at Cathédrale, a brand-new French-Mediterranean restaurant by Tao Group (the hospitality company behind restaurants and nightlife spots like Tao, Lavo, Avenue and Marquee). The expansive space has two bar areas, a private back patio, a stage-adjacent dance floor and, on Thursday night, more cobwebs and other Halloween decorations than we could possibly quantify. By definition, the event made for top-quality people-watching. Some of the costumes we marveled at most: “Lizzo” with a wedding dress and flute, a paleontologist with a “skeleton” in tow, the Fairly Oddparents and a couple dressed as Bob Ross and his landscape painting. 

Some of the best celebrity costumes we laid eyes on? Queer Eye’s Antoni Porowski and his date dressed as zombified Blockbuster employees, complete with popcorn, VHS tapes and cobwebs stuck to their outfits. Model Coco emulated Madonna with a gold corset and cone bustier, and Queer Eye’s Jonathan Van Ness appeared as a tiger. Dylan Sprouse and model Barbara Palvin chose characters from Princess Mononoke. 

Theme cocktails were sponsored by SVEDKA Vodka and had names like ‘Til Death Do Us Party, Soul Taker, Bloody Sunrise and Just My Blood Type (served a drinkable “IV packet”). Guests could also take part in a production experience sponsored by Amazon Prime Video, in which they entered a film set designed to look like a cult headquarters (complete with hooded figures and an array of candles), were filmed via multiple takes on via professional-grade camera equipment and, afterwards, received their own 20-second short film. 

Klum tapped Questlove as DJ for the evening, and he opted for a rotation of wedding favorites — Sister Sledge’s “We Are Family,” Wild Cherry’s “Play That Funky Music,” The Bee Gees’ “Stayin’ Alive” — that had nostalgic guests swaying on the dance floor. Two private party areas — the back patio and an area beside the stage reserved for Heidi’s close friends and colleagues — required a special wristband to enter, and tables were all reserved for VIPs. Unfortunately, that meant the only place to sit down and rest was the bathroom, which, if you’re in high-heeled boots, means you may have to go barefoot for part of the night. (Spoiler alert: We did, and if you’ve ever spent four hours in three-inch stilettos, you’ve likely done the same.) 

Klum staged her dramatic entrance just before midnight, and people pushed and shoved to snap a photo as she descended the red-lit staircase. It was easy to forget that no one in the venue had purchased tickets to Klum’s party; she puts on the invite-only affair each year with the help of partners and sponsors, though decades ago, she likely put her own money into throwing the bash. Klum has said her prime reason for throwing the event is her passion for Halloween and giving people a reason to dress up and have a good time, but it definitely comes with some perks that could translate to business opportunities down the road: In many circles, her name has become synonymous with Halloween, and the party offers her a great chance to showcase her creativity, spontaneity and humor with everyone from close friends to potential business partners. 

We left just after 2:00 a.m, after we deemed we’d made enough small talk with cowboys and hippies, and some dedicated priests and New York Yankees players were still tearing up the dance floor. Late in the evening, Klum was served enormous cake topped with figurines commemorating each of her Halloween costumes from the past two decades. Odds are that alongside her business planning meetings for 2020, she’s already started brainstorming next year’s Halloween costume.