Hey there nerdinaskirt, aka my second pick for a name :P
We’re all scared when we go out the first times. In fact, when I go to certain places wearing certain things I’m still scared of assault or, on a less physical note, embarrassment or exile. It takes a lot of courage to say, “Who says skirts and dresses are just for women? And on what authority did they say it?” That courage seems to make people uncomfortable, makes them have to question the society they thought was so clear cut on this whole gender thing. Sometimes, our courage makes people so uncomfortable that they lose control and lash out. The key, in my opinion is avoiding those situations.
And before I give advice, I’ve never been attacked in public for wearing a dress, dirty looks, sure, but never assault. It’s 2014 and Pittsburgh is liberal enough to not lynch the Hairy Jew in a Dress anymore. The biggest response I get, beyond not being noticed in the first place (for sure #1, I mean, people have cell phones), at least in my college setting is praise, compliments or questions.
So I guess the first piece of advice is pick your setting. My liberal college is a safe space for this here queer. No one in my clubs give me shade (save for over-wearing an outfit), no one in class talks crap to my face, even if I’m sure they want to (Guess who has more courage now!?). Shopping centers are a safe place too, especially since they want you to buy their stuff, and’ll probably compliment you. Over time my Hillel has become a safe space *more on that in a post about Judaism upcoming.*
The second is to have your supportive friends with you. Safety in numbers for one, but secondly, they’ll push you to actually go out and be in the world. I have a roommate who dreads as much as he looks forward to the fight that he *knows* is going to happen over me in a dress; while I have trouble seeing it happen now that I’ve been at it for over a year, I’m comforted knowing he would fight with/for me. Eventually, I felt just as comfortable walking back from the bar along in a dress than I did with a friend during the day, but it takes some time, and actual evidence that the worst that’ll happen is cat calls!
Third, dress in clothes you’re proud of, an outfit that gives you confidence. People might laugh, but the ones that don’t’ll be the ones that see how much work you put into finding the skirt/shoes/etc that made you look incredible. It’ll also make it more clear that what you’re doing is intentional and not a joke or prank.
I’ve found that wearing a smile and answering why you’re in femme stuff jovially, helps others to be jovial about what you’re doing. Hard to keep the disrespectful or confused look on your face when the beardo in the dress gives you a huge grin!
I hope any of that helps. The biggest way to erase the fear is experience. The more you do go out in the things you really want to wear the more comfortable you’ll feel. And hey, the more of us out there doing this, the more people’s perceptions and expectations’ll change and the thought of being attacked for wearing a dress will be quite laughable!