After having felt the freedom of a dress and the wind against the bare skin of my legs, it was weird putting on pants again. Let me premise this; I am not a transvestite nor am I transgender, I am simply a man who wore a dress on Halloween, and later realized that it made a great social experiment.

To give my dear reader some back story, I purchased the dress at a thrift store with the help of some friends who are more experienced in the field of dress shopping and wearing then I. The dress was to be part of a group costume. The aforementioned friends and I enjoy Contra dancing and the Contra before Halloween was a costume Contra. My friends wanted to go as fairies and convinced me that I should be the Fairy God Mother, and where a dress, because “Dancing in a dress is so much fun, you can twirl!” I acquiesced and and thus I now have a dress.

Dancing in a dress was a lot of fun, especially once everyone had seen me. The most frightening part of wearing anything new is seeing how others will react. And every one at the dance loved it, so I was feeling great and my friends convinced me that I should wear my dress on Halloween as a costume and attend all of my classes that way. Thus begins our story.

So my one stipulation to this plan was that one of my friends meet me outside my dorm room to walk with me to class. Because being alone, in a dress, as a guy, starting the day, would be terrifying. I was okay after I built up confidence, but the initial step into public was terrifying. It is interesting that we always tend assume that others are thinking the worst of us, even if we have no reason to think so. This is why trying something new alone can be hard because there is no one to be with, and one assumes the worst from everyone else.

So we walk to our first class and I get a mix of responses. Some say I am beautiful, some do not like it, and many say I am brave. And this is what surprised me, the amount of acceptance I got throughout the day. I go to a very christian college, and thus I was nervous about how our population would react to a male in female’s clothing. But the majority were fine with it, and some quite enjoyed it. I think part of this is due to it being Halloween; people were much more forgiving of one's choices of dress. Several times I got asked, “So is this for Halloween? Or is it … ?” to which I always replied, “Yes, of course it is for Halloween,” and then proceed to tell them the story.

But I wonder what the response would have been on a day that was not Halloween? Would folks have been as accepting? Why is a man wearing a traditionally female garment so appalling? And why do we ascribe clothing to certain genders to begin with? Why is it more permissible for a woman to wear a pants suit then a man to wear a dress? And how and when did this strong differentiation between women’s and men's clothing begin in the first place?

If there is anything I have learned form the experience, it is that one should go for it and take chances. They will often turn out better then one is expecting. And another key piece of insight I gained, dresses are very comfortable and very fun to wear.