10 iconic Halloween costumes, spanning glam, grotesque and... WTF is that?

The smell of Halloween might be in the air, but this year it’s looking kinda different (duh). Where celebrities usually excel at throwing wads of cash at the situation, not a pot of papier mâché in sight, 2020 is feeling a lot less spooky – thanks, in part, to the simple fact that switching on the news (or Emily in Paris) is far scarier than the Candyman et al could ever be. 

Since we won’t be getting our usual serving of Heidi Klum in full-body prosthetics, dressed as a completely bizarre cultural reference that sees everybody at the party whispering “Ugh she always upstages everyone, classic Heidi”, we look back to the heady days of yore, at some of history’s finest Halloween moments. 

Some of them are gorj, some of them are gruesome, but the best part, without a shadow of a doubt, is Michael Kors holding an apple. Reader, let’s begin. 

NEIL PATRICK HARRIS AND DAVID BURTKA AS THE OLSEN TWINS  (2019)

Consider me deceased – the cigarettes, the all-black everything luxe rayon mix with the dirty blonde hair and, of course, the signature Olsen Twins wake, but make it fashion energy. Bottle it and I’ll buy it. I once heard when they’re at a party (the OG twins, that is) they have a secret hand language so they can express their boredom to each other without having to say it aloud. Bottle that, too. But back to the look. It’s camp, if not out-and-out gay, and it’s fashionable by association. What more could you want? Tbh, an XXXXXL coffee in an environmentally irresponsible plastic cup wouldn’t have gone amiss, but great work nevertheless. 

Spooky rating: 3/10 – Iconicity rating: 9/10

HEIDI KLUM AS PRINCESS FIONA FROM SHREK (2018)

Klum, as we’ve covered previously, is famous for her Halloween looks, with turns as a butterfly, a transformer, and Jessica Rabbit under her belt. But Princess Fiona is particularly inspired because Klum is speaking to the ogre in us all. This is the kind of hallowed(ween) representation I’m seeking. From the dress and the prosthetics to the wig – uglification is a bold move from someone who has never been ugly – like, remember that time Niccy Kiddy won an Oscar for sticking on a fake nose? – so the guts that this must have taken are really the kind of inner strength I’m looking for in my Halloween offerings. 

Spooky rating: 4/10 – Iconicity rating: 8/10 

WINNIE HARLOW AS RUPAUL (2018)

Drag is to gender what mayonnaise is to a sandwich: essential. And so it’s thrilling to have Ms. Harlow remind everyone that anyone, as long as you’re not a dickhead, can mess with theirs. And while RuPaul may have fallen down the iconicity scale thanks to a series of ‘incidents’ *cough*fracking*cough*trans-exclusionary comments*cough*, Harlow took it back to Mama Ru’s heyday and the 1994 Viva Glam campaign which, let’s be honest, was 10/10 iconic. 

Spooky rating: 3/10 – Iconicity rating: 7/10 

CARDI B AS CRUELLA DE VIL (2017)

We love nothing more than a deranged wealthy woman who wants to murder 101 puppies in the name of a coat. Hell, that’s why I got into fashion. Of course, as time has passed, we realised just how simultaneously dark and misunderstood Ms. de Vil is, and in classic Cardi fashion, she is here to represent the underDOG – those who have been misunderstood and misrepresented. This is the kind of fur-lined brilliance we love to see, dalmatian included, but if we’re going to be anal about it, one point deducted for the lack of a press-on nail atop the famed red glove. But, as Cruella learned when those pesky middle class heterosexuals eventually got their puppies back, we can’t always get what we want. 

Spooky rating: 3/10 – Iconicity rating: 9/10 

RIHANNA AS A TEENAGE MUTANT HERO TURTLE (2014)

The costume isn’t even that good, but she just can’t put a foot wrong. Honestly, I just can’t fault her. Aside from saying I just want new music at this point: come on RiRi, we need it. 

Spooky rating: 3/10 – Iconicity rating: give us an album and we’ll give you a score 

MICHAEL KORS AS THE GARDEN OF EDEN (2017)

My editor told me not to include this, but frankly, we needed one scary costume in here, which this quite clearly is. I don’t quite understand what’s happening, but this is perhaps the first piece of MK I’ve been desperate to own (since I ditched my first ever mushroom coloured crossbody way back in 2010). Michael has really nailed the metaphor here: him wrapped in a snake while holding an apple, and while  I fantasise about the number of people who asked him ‘what are you supposed to be?’ thus forcing him to stand back and say “A SNAKE??? An APPLE???” as they ruminate... ‘are you Blackpool Zoo?’ before he finally addresses the elephant in the room and reveals himself to be the original sin.

Spooky rating: 100/10 – Iconicity rating: 100/10

ORLANDO BLOOM AND KATY PERRY AS DONALD TRUMP AND HILLARY CLINTON (2016) 

The year was 2016. Hopes were high. The US election loomed. In a very on-the-nose stunt to prove to the nation that they were not Republicans without ever having to actually say it, Perry took on Hillary while Bloom lurked in the background as an overgrown, grotesque effigy of Donald Trump, languishing in the shadows as we expected him to do as the results rolled in – but reader, we all know what happened next. With November 3 fast approaching, we’re hoping the pair’s Halloween curse is finally lifted. 

Spooky rating: 8/10 – Iconicity rating: 5/10

KATE MOSS AS CARA DELEVINGNE (2014) 

One can’t tell if this costume is an homage to or critique of Ms. Cara Delevingne, but what we do know is that there is enough chaos in the image to keep us satiated without ever finding out. The ‘rock on’ fingers, the tongue hanging from the side of the mouth, the sunglasses… the sus white powder lightly glinting on the end of her nose: it’s the evolution of the modelling industry and everything it ever was captured in one chaotic image. We stan. 

Spooky rating: 10/10 – Iconicity rating: it’s not quite up there with calling an airline pilot a basic bitch, but it’s still extremely iconic

KIM KARDASHIAN WEST AS POISON IVY (2011)

There’s a deep irony to Ms. Dashion’s turn as Poison Ivy. See, I’d wager that Kimmy’s carbon footprint is among the top hundred in the world and while Poison Ivy was derided for her evil ways, her intention was in fact A Green New Deal. To replant the forests of the world. To stop climate change. Now Kim has done some good stuff in her time, but methinks a TV which rises from the floor and a mass produced perfume bottle pressed with million year-old sand torn from some coral reef somewhere is not exactly going to do much for the planet’s quickly diminishing ice caps. That said, it’s the truly 2011 tan tights that are the true horror show when it comes to this look. 

Spooky rating: 4/10 – Iconicity rating: : S 

ROBERTO CAVALLI AS KARL LAGERFELD (2007) 

A wise man once said dress for the job and the salary you want: Bobby C was clearly listening. 

Spooky rating: Forest print beach kaftan – Iconicity rating: Forest beach print kaftan

Want more Halloween stuff? Check out a spooky watchlist compiled by your fashion faves in the gallery below.