Why Every Man Should Dress in Drag at Least Once

I never really had the desire to dress up as a woman. For years I had a hard time understanding why some gay men were so obsessed with drag.


Photo courtesy David Bonner

This Halloween I was in drag for the second year in a row. A friend initially prompted me to do it, and I loved it so much the first time that I decided to do it again.

Something happens when you put on a dress, a wig, and some makeup. Your personality transforms. You just can't help it.

It was a hoot, but it also served as a teaching moment. I think every man -- gay, straight, or in between -- could benefit from a day in drag. And here's why:

More Empathy Toward Women

Growing up in a house with a mother and two sisters, I watched as they applied makeup every day, not thinking much of it. I didn't realize what was really happening. They were painting on a face every single day. On Halloween I found out just how long a process this is. And don't get me started on the heels. After just a few hours in low heels, my dogs were barking. I can't imagine spending an entire day in stilettos. It's torturous!

Feeling Pretty Feels Good

Some men are used to hearing terms like "handsome," but being told you are pretty is pretty awesome. I received a lot of compliments among the West Hollywood crowd, but I was touched when half a dozen women throughout the night looked me in the eye and told me I was truly beautiful. How's that for a self-esteem booster?

Feeling Like a Star

Dozens of people from all walks of life wanted to pose with me for a picture. There were so many flashbulbs it felt like the paparazzi were there. It was as though I were on a red carpet. This was great for the ego and gave me a tiny taste of celebrity.


Photo courtesy David Bonner

Feeling Free

Dressing up in character allows us to switch identities and loosens up the inhibitions. It allows us to say things we might not otherwise utter in our more reserved lives. It allows us to be bold and approach people we might otherwise find intimidating. Though we're in character, dormant parts of our personalities start to emerge, and I believe that's a good thing.

Flaws Are Forgiven

When you dress in drag, people like the campiness of it. They admire the boldness it takes to get into character, and I find they forgive your flaws. If you have a little extra fat around the waistline, it doesn't matter. If your arms are hairy, they expect it. If your makeup isn't perfect, they embrace the effort it took to slap it on. In a world where we are so critical of others, it's nice to get a pass. And when men put on dresses for Halloween, they're given that pass.

I won't be competing in RuPaul's Drag Race anytime soon, but I am looking forward to picking out a dress for next year. I'll be smarter too and wear flats!