I had never heard of Dressember until I received an email from Chris Dorso who is raising money for charity by wearing a dress every day (in male mode) for the month. I asked Chris to write a little about Dressember and I am excited to share what he’s doing. Please consider donating.
I stumbled on Dressember late last month after a number of friends did Movember fundraisers, and thought, “ooh, this looks like I could be a lot of fun.” The Dressember Foundation raises money and awareness for the prevention of trafficking, along with intervention and protection of victims. I was a little wary because I really knew nothing about the charity, but Guidestar and Charity Navigator gave it their highest ratings, so I figured it was safe to say that the funds raised would go where they were supposed to go.
The next challenge for me was finding dresses. I’ve done drag on stage, and I’ve worn female Halloween costumes over the last few years, so I had a small stash of dresses and shoes and tights in my closet, but I figured I could probably reach out to friends for help too.
I registered for the event and built my landing page and sent it to my wife to see what she thought. She’s generally been really supportive of my crossdressing Halloween ideas, but a whole month, especially considering the holidays, was probably a heavier lift. Her opinion and comfort level is really important to me. Thankfully, she said it sounded like a fun idea. Her one caveat – “you’re not stretching out any of my dresses!”
I then sent the link to a few local friends and asked if they would be willing to help. They jumped on board immediately, and that day, I ran around town picking up bags full of dresses they were going to donate anyway. I’ve had friends from literally all over the country send me stuff to wear, which has been fantastic.
I set my goal at $500 — I figured if I encouraged folks to just give a few dollars each, that was probably a safe goal. I posted a picture on social media on the afternoon of December 1, along with the Dressember story… and by the following morning, I’d blown past that goal!
My boss donated. My colleagues donated. My sister donated. My in-laws donated. Friends from high school and college donated. Friends of friends donated. Response to my pictures — a bald guy wearing dresses — were unbelievable. Fridays are “Fancy Fridays” for Dressember, so on Day 4, I pulled out a short red dress that I got at a thrift store and a pair of over-knee boots and took a picture next to our Christmas tree — and donations absolutely exploded!
As of this writing, I’m already in the top twenty of all participants on the Dressember main site, and the whole experience has just been absolutely incredible. And the best response has been from my kids. They’ve both been wildly supportive also, and that has absolutely meant the world to me.
Ultimately, wearing dresses is super fun. They’re colorful, they’re comfortable, and ultimately, clothes don’t have a gender, and what I’m wearing is entirely my business. I’ve gotten some looks as I’ve been out and about, and I’ve become quite comfortable to meet every one of them with a nod and a hello.
I’m excited for the rest of the month. I’ve got a few more Fancy Fridays, plus Christmas and New Year’s, and I figure if I keep pushing the envelope every time, I’m going to raise a lot of money for a great cause.