Why Halloween Is the Perfect Time for Self-Expression

“Halloween gives people permission to engage in boundless creative self-expression.”

Halloween holiday frame in orange background.Flat lay
Halloween holiday frame in orange background.Flat lay

After facilitating my company’s leadership meeting last week, I found myself enjoying dinner with five co-workers. Three were relatively new to the organization, and instead of talking business, we thought it would be fun to ask “get to know you” questions at the table. When I asked this group of primarily 40-somethings about their favorite Halloween costume of all time, the look of delight on their faces was priceless. While a few people talked about childhood costumes, most focused on creative get-ups donned as adults. And that’s when I realized that, as grown-ups, Halloween has really become about creatively expressing ourselves.

Sure, Halloween is ultimately focused on kids. I loved seeing photos on Instagram and Facebook of friends’ children dressed as heroes from The Incredibles, or a toddler Kermit the Frog, or as Minions and Ghostbusters. It was one of my favorite holidays growing up, from picking my costume to planning the consumption of our Halloween candy haul (mini Reese’s cups were the best, so I inevitably dug into those first). But college took Halloween to a whole new level. I’ll never forget Emory University’s Halloween Ball my sophomore year, where we danced for hours as the 1980s one-hit wonder Men Without Hats provided the entertainment. I went as a Chiquita Banana, which was achieved by wearing a fluorescent yellow dress, making a headdress with fake fruit and creating a Chiquita logo for my stomach and back. Fun-size candy options were still aplenty. But hanging out with buddies before heading out, crafting a costume that inspired lots of praise and then dancing for hours without a curfew now infused the holiday with a heady sense of freedom and creativity.

Yesterday, I caught up with a friend taking a cardio walk around a local park. Her sons are both in high school, and Halloween has come full-circle again for her and her husband. They found themselves staying out late Saturday night at a party with their adult friends having a blast. Her spouse, who avidly embraces fitness, went as a Gladiator, while she went as a Roman Princess, showing off the hard work she has put into getting into shape herself. These were the kind of outfits they’d never wear except during Halloween.

Over the years, I vacillated between creative highs and repeat outfits that happened to look good (mostly when I was single and dating). For example, in 1995 I had to buy an expensive floor length red gown for a special event. So, I decided to reuse the heck out of it to justify the cost. One year, I donned long white gloves and went as Julia Roberts’ character from Pretty Woman, while a decade later it was repurposed as a Miss Congeniality costume, where I channeled Sandra Bullock. My favorite costume of all time, though, was a homemade affair expressing my love for pop culture. Remember Chia Pets? I went to a party about 15 years ago as a “Shira Chia,” which involved creating a sandwich board wrapped around my body where I drew black plugs filled in with cuttings of fake plants.

Madonna might have been preaching a daily practice when she sang “Express Yourself” nearly 30 years ago, but that’s easy to do when you are an international pop icon. But for those who are more buttoned down than the Material Girl — which is kind of everybody, right? — Halloween gives people permission to engage in boundless creative self-expression with their costumes and behaviors.

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