Fashion And Beauty Insiders Share Their Most Memorable Halloween Costumes

Betsey Johnson, Sir John, and more

There are people who are really good at Halloween, and there are people who are… not. (There are also those who just don’t care, but that's not the point right now.) Those people who are good, though, are really, really great, and can just as easily plan their costumes months in advance as they can think up something on the spot; either way, they still manage to out-costume everyone else. These are the Halloween enthusiasts, the creatives, and usually (but not always) the people whose jobs involve playing dress-up for a living.

We’re talking fashion and beauty insiders: designers, makeup artists, stylists, and artistic directors. Sure, celebrities are the ones who usually get the attention for their costumes, but you know who’s usually behind them? These people—who also happen to have their own arsenal of impressive costumes themselves.

And so, with the spookiest night of the year approaching, we decided to ask designers like Kim Shui and makeup artists like Nick Barose to share their favorite getups, some of which include Lil’ Kim, Brad Pitt from Fight Club, and, simply, Yves Klein Blue. Get inspired by all their ideas, below.

Sir John, L’Oréal Paris celebrity makeup artist

I was never able to participate in Halloween when I was younger as my mom didn’t really believe in dressing up for the holiday. That all changed when I went to college though! My favorite costume was when I was Brad Pitt from Fight Club. I was in the gym and very into weightlifting, so I fit the part! I created bruises with makeup on my body and really looked like I just stepped out of the movie. My mom even saw me that night and believed the bruises.

Kim Shui, designer

One of my favorites was probably a Lil’ Kim outfit from her “Crush On You” video. It was all blue, I had a wig and all. Not many people were able to identify who I was, but some did! I chose it because we had made these gold-plated K earrings earlier that season and was inspired.

Nick Barose, celebrity makeup artist

Buster Keaton is one of my favorite funny men along with Charlie Chaplin. This was a last-minute costume, so I pulled something from my closet—the polka dot vest and vintage Versace also added to the clown effect. I usually get so involved with costumes, and though it’s fun to do full-on drag costume, it takes lots of planning. I painted my face with foundation that’s a lot lighter than my skin, then I rubbed it in a bit to make it a bit blotchy; you’re not going for pretty here. I painted my brows in darker and smudged plum lipstick around my eyes and defined my lips like how the guys used to do in the silent films era. You can do slapstick things like spill drinks, trip all over the place to get in character.

Kelli J. Bartlett, Glamsquad artistic director

I absolutely love Halloween as a makeup artist… but, by the time it is time for ME to create my own costume, the last thing I want to do is a sparkly, glittery sexy costume. That is why, every year, I dress as a guy! My favorite would be when I dressed as Uncle Sam. It was an election year, so I wanted to do my part in spreading the word and getting people to vote!

Betsey Johnson, designer

I have been hooked on my skeleton costume for years. I was a skeleton over and over and over again, so this year I decided to choose something new because I just couldn't be a skeleton anymore! So, I walked into my closet to find inspiration, and I found this yellow-and-orange striped sweater from the '70s. And now, I'm a candy corn. Best part is, my 10-year-old granddaughter is doing my makeup! She's been studying theater makeup after school. I have always loved Halloween as a holiday, dressing up and all that, but now it is all about me and my grandkids.

Adam Vanunu, founder of Cotton Citizen

Yves Klein Blue is my favorite color—I have an obsession with blue like he did, which is why you see a strong blue hue in every Cotton Citizen collection. I got my costume inspiration from my color inspiration. Yves Klein did a very famous performance art event in Paris in 1960 where he had his muse paint her body in blue and transfer the paint to canvas, which is where his “Anthropometry” paintings came from. My girlfriend and I recreated that iconic moment for Halloween.

Marta Goldschmied, denim designer

Courtney Love has always been an inspiration to me. She’s the princess of grunge and a poster girl for rebels like myself who always felt like the black sheep. When my friends and I decided to all dress up as music icons, Courtney Love was my obvious choice. It also wasn’t that hard because she truly is my ultimate style inspiration. Paying homage to Courtney was so much fun, and something about being all in costumes always makes for a magical night.

Heather Newberger, stylist

My favorite Halloween costume was some years back when I first moved to New York City and dressed as Corinne Burns, Diane Lane’s character from Ladies and Gentlemen, the Fabulous Stains. I wore her off-the-shoulder, red see-through blouse, black tights and threw my hair up like a skunk, using a washout dye to paint the sides white. I practiced Corinne’s eye make up for days before, and probably got about 75 percent of it right. I am a fashion stylist and not a makeup artist, after all. 

I never got a picture of the look, but I was so excited about it that I made Corinne my Facebook picture for the month of October. Days after Halloween, my grandmother called my parents to ask if I had lost my mind. She’d seen the picture, and could not believe I’d dyed my hair black and was wearing so much red above my eyes. To this day, it still makes me laugh that someone who helped raise me for all of my life could think that, at 22, I looked much more like a 17-year-old Diane Lane than myself.

Sara and Jaron Kanfer of UNKNWN

We threw a Studio 54-themed party and dressed as Tony Montana and Elvira Hancock [from Scarface], mixing themes slightly. It only made sense to pay homage to Miami Beach's disco fashion royalty.

Rebecca Minkoff, designer

I’ve dressed as Frida Kahlo for multiple years, and it’s always my favorite! She’s a trailblazer, an inspiring woman, and we both have dark hair–win, win!