As to going out in public, I'm sure this is a much more emotionally-charged issue for you than it is for anyone who'll see you. Just pick a location, wear something plain, stop sweating bullets, and do it. Expect to get some second glances but no hostility. Think of it as counter-cultural or self-assertive, like long hair or earrings, and not as fetish-dressing or perversion. The vast majority of people will just shrug it off, as they do for people wearing all sorts of crazy things. As to the rest, that's their problem and not yours.
If it helps, pick someplace out of town where nobody knows you. For the anonymity of a crowd, pick someplace large like a shopping mall. Or if being seen by so many people at once is scary, pick someplace small, like a coffee shop or convenience store. It may help to have a number of places planned, like a gas station, one or more small, shops, and then a grocery store. If taking out the garbage or bringing in the mail is the most you can do, start with that, then graduate to driving around, and then to getting out away from home. See how far you get and then try for more next time. Just stand tall, assert your right to individuality, and don't give up
To cut down on the visual discontinuity, you may want to pick a style, fabric, and color that resemble men's garments -- a cargo skirt or kilt that resembles cargo shorts, for example. But above all do be yourself, stay positive, keep up your nerve, and don't shrink, sweat, skulk, or stammer. Just relax and do it.
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Your name is interesting in that a scooter is a combination shorts/skirt without a rear apron
and a predecessor to the Skort which has both front and back aprons.
I wear kilts skirts and skorts and I likem "short" !
The skort unlike a kilt or skirt has a built in modesty factor - the shorts hidden under the apron.
The are some here who decry the skort as being like a heresy of sorts due to the bifurcated
item worn within. But then you are not going to be cited for immodesty when you have things covered !
With the skirt and kilt worn short one must be on guard for ackward moments - but then a fleeting
glance never hurt anyone and is sure to please someone.
So I take it that you have more than the scooter in your wardrobe ..... ?
Again Welcome aboard and tell us about skirt wearing in the "Big Sky" country !
Isn't wearing a kilt enough?
Well a skirt will do in a pinch!
Make mine short and don't you dare think of pinching there !
The first time out is always the hardest, good luck with that. I found that my own fear was the only thing holding me back, once I conquered that it has been all plain sailing. The worst I cop is a raised eyebrow and the odd second look.
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Best of luck, and I hope to see you out there soon!
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You've had some bits of good advice and I'll second the motion to just get out there once, and then it will be easy after that and just get better and better. Based on my experience, I'd suggest just walking around a bunch, either in a park, city streets, a walking trail, or other place where there are quite a few people. You will find that you'll hardly get any obvious attention. Maybe people will be noticing you, but as you walk you won't be turning your head to see their reactions. Then try interacting with someone, say by buying something in a shop or restaurant. You will be treated just like any other customer. You will be thinking about your skirt the whole time, understandably, but others won't be. Just have fun, live in the moment, enjoy life and your new freedom!
When the time comes (soon, I hope) to be skirted among friends and/or family, start out wearing a kilt, traditional or modern; you will look different, but a kilt can always be explained as made for men. But any conversation that develops should focus on the comfort aspect; and you could go into the "fashion freedom" argument about women & pants, the unfairness that men are limited by society but women can wear anything, etc. As the weeks go by, you can incrementally shift from kilts to plain skirts in "masculine" colors, then to ones with a bit more femininity, if that's what you would really like. Make it a very gradual progression.
Throughout all of this, be happy and confident. This will be a fun thing to do. Don't worry, just do it!