jc.33 wrote:Caultron, it's a mix of both of what you said. Confidence is very much spoken about here of which I am lacking. I'm very much an introvert so finding the courage to go against the grain is very out of my comfort zone.
Step one is probably to get used to the idea yourself. Go to a thrift store and buy a few skirts in whatever styles you're interested in, They'll probably cost about $5 each. If you don't know your size. either use the fitting rooms or bring a tape measure and measure the shirt inside the waist. LIke, if you wear size 34 pants, look for a skirt that measures about 17 inches from side to side inside the waist.
Shopping will probably be nervy at first, as if you're not
supposed to be in the woman's department. If so, it may help to have a cover story ready. That way, in the unlikely event that someone asks you, "What are you doing in the women's department?" you can answer, "My wife isn't feeling well but asked me to pick something up for her," or, "My girlfriends wants some grungy clothes for her birthday," or whatever.
As to the fitting room, just use the same one you'd use for a pair of shorts. No one is going to pay much attention to whatever garments you have under your arm. But if that's too much, just buy a few different sizes, take them home, and return the ones that don't fit.
Just wearing a skirt might seem odd at first, and looking in the mirror might convince you that you look ridiculous. But just keep it up and get used to the feel of it and after a while it'll start to seem more normal.
It may help just to look at photos of men in skirts. I'm not talking about men impersonating women (usually with terrible results) but about men wearing a skirt of kilt and still looking male from the waist up. Even those photos may seem strange for a while but eventually you'll get past it. It may also help you choose your style.
If all you can do is go outside in the back yard at night, do that. Then, after you're convinced the world didn't end, try the front yard at night or in the early morning. Take out the trash, or pick up the paper, or something. You'd do it in a robe and a skirt's not much different.
Buying gas or picking up a convenience store item seem to be popular first experiences, perhaps some distance from home. When you become convinced there won't be any fashion police, black helicopters, or circles of people pointing and laughing, graduate to longer and longer outings with more and more people around.
The first skirt I wore in public was a utility kilt, and I wore it to a tattoo convention, which had the advantage of being a fairly countercultural place anyway. There's just a lot of freaky people walking around looking at all the other freaky people. But if that's not your interest, perhaps another countercultural event would do: an art show, a comicon, a rock concert, or something like that.
Just keep at it.
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