What Billionaire CEOs’ Halloween Costumes Tell Us About Them, According To A Psychiatrist

Costumes are part of Silicon Valley culture, from the carefully casual jeans to the ‘I’m too cool to care’ hoodies. But when Halloween rolls around, CEO’s are happy to switch it up a little; think eye dropping excesses and tongue in cheek pop culture references.


This Halloween, Warby Parker cofounder and CEO Dave Gilboa was resplendent in a human sized peanut suit — a cheeky tribute to Planters salty snacks. And his jaunty cane was additionally helpful in keeping his balance, post a recent ACL surgery.


Every sartorial choice people make tells others about the inner workings of their life — and this holds true in the Silicon Valley tech CEO world too. Whether it’s reading something into Zuckerberg’s affected lack of affectation with his gray t-shirt uniform or Marissa Meyer’s tailored power dresses — fashion plays a part in how people define themselves and their work habits.


However, a Halloween costume is a chance to reinvent yourself — regular people might choose to play at Batman or Wonder Woman, but what does it mean when a CEO’s sartorial choices mimic this as well. It’s fun to read into what they’re wearing, and hey, we all need a little bit of fun right now.


“Many people really enjoy dressing up in costume because it’s a way to try on a new identity and have fun with that identity,” Dr. Gail Saltz, a New York psychiatrist and the host of, “The Power of Different” podcast told me. “People often choose someone they admire or wish they could, even for a little while, embody.”


With her help, I took a look at some of the interesting wardrobe choices made by techies and CEO’s this Halloween.Neil Blumenthal decided to embrace the Halloween spirit, by wearing two costumes. One outfit was a family costume, where he wore a Darth Vader suit (his son was a Stormtrooper) and the other had him dressed as a ballerina in a white tutu (to his wife’s Black Swan).


“More than one costume is an extra opportunity to try a new identity and may be driven by the audience who they feel will appreciate the humor, or extravagance, or whatever of their identity versus another audience which would ooh and ahhh about something different,” says Saltz.Mark Zuckerberg is known for many things, but Viking prowess..not so much. Which meant Halloween was a perfect opportunity to wear some armor and dress his daughter as a baby dragon.


“Costumes and dressing up are also a way to bond with others and define yourself as an unit. This might be a family unit or friend or colleague unit or couple unit. It creates an automatic feeling of we belong together, and we are set apart from the rest of you,” says Saltz. Saltz says that costumes like a Viking group can be wish fulfillment — hoping their child becomes part of a fierce Viking-like group.Dennis Crowley and his wife dressed up as black-suited bodyguards with matching earpieces and sunglasses to accompany Baby Hillary Clinton around their neighborhood. The outfit adheres to Saltz wish fulfillment analysis of costumes – she says that a political style like this is a wish for “my daughter to become strong and successful like Hillary Clinton.”

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