JoePublic wrote:I dread my first trip outside. Even though we have the weather for it.
This is going to sound trite, and I know it, but it's a heck of a lot easier than you might think. Yes, you're going to buck conditioning you've been receiving all your life -- and that can be terrifying -- but, in the end, really all we have to fear is the fear itself and a small dollop of the unknown.
It'll go easier if you're reasonably well-practised wearing a skirt, and the only way to get that is to do so. When you're learning, sometimes it's best to do so around the house and out in the yard so you'll know how the skirt will behave under certain situations (and they do not behave the same way as trousers) so you can properly manage the thing and not be flustered when it does something unanticipated. Simple rigs like knee-length denim skirts are the easiest to start off with just to "get the hang of it" (bad pun, I know); once you've mastered the basics you can -- and should -- move on to developing a look and style your own.
The most important thing with being out and about in public is your confidence level. People pick up on that. They'll also pick up on things if you're obviously fighting with your clothing because you don't know how it'll behave. When you're ready, take a deep breath, gather your thoughts, and head out the door with your head held high.
" I also got a few "You know, if you wear something under a kilt, its just a skirt at that point" and I would replay, "Good thing it was a skirt to begin with so I don't have to worry about that", or "jokes on you, if I took these legging off it would still be just a skirt". 
but if I was to wear it with out the leggings then yes.
