I have found this thread by chance having been offline for about a week. It is normal practice for me to consider all comments and opinions before adding my own and unless I missed it, I didnt see anything regarding the question of confidence when it comes to wearing a skirt.
Firstly, I have found that shyness is not compatible with transitioning rather being a transsexual is the best cure for shyness because we have to endure so much in order to get to our final destination.
Secondly, our own opinions of self play a huge part in how we present ourselves to others. I have found that a majority of contributors are committed skirt wearers even in the colder climate that is Canada but I failed to find anyone hostile to skirts. I have had furious rows with a TS friend about skirts, she insists they are stupid garments and does not need to wear one to prove she is female etc, it is her opinion and I respect it.
I count myself as someone that detests jeans, too stiff, structured and unforgiving to my skin. However I do wear pants/trousers as and when I feel it a good idea. My wardrobe has about 6 good pairs that I could wear formally or leisurely owing to the fact they are comfortable, soft fabrics and look good. I have well over 50 skirts but most of them do not fit just now, my waist line fluctuates so much I cry over the cost of replacing them. If I had 500 skirts, I would probably be unable to find the right one to wear

I mentioned earlier the matter of confidence. I was three months into my transition before I smashed the 'skirt barrier', an event that occured by accident owing to an accident with some coffee. With no spare trousers available, I was forced to wear my first skirt in public and wondered what the fuss was about. I then went through a spell of wearing only skirts and I must have looked bloody aweful to those that saw me. My makeup skills were elementary, I had yet to accept I needed to wear a wig owing to hair loss ( I wore headwraps/bandana's ), and struggled with suitable shoe selections. I was living in a bubble of my own making and felt invincible.
One day, during a routine hospital checkup, my bubble burst. I became aware of how badly I was 'passing', I was aware of everyone else clocking me and felt terrible. I retreated back into trousers with a feeling that I let myself down and the wider TS community for being bullied back towards malehood. After many changes in my approach to transition I rediscovered the pleasant nature that skirts offer to the wearer, something that only women understand. I still wear trousers to certain places i.e rehabilitation sessions at the hospital ( stroke revovery excercises ) for dignity and modesty reasons, I have to wear a skirt for formal reasons when working at the theatre, and I now wear skirts for the fun of it to go shopping because I now feel confident again that I look almost womanly again.
Details such as hair removal on the legs, temperatures, waistlines, the right top, and shoes whilst important, are just details. The key for me has been confidence, to go out there and be myself, be the woman that I truely believe myself to be and hang the rest of the world if they dont like it. As Cindybc said, "it's nice to dress up whenever one feels like it, we do not need an excuse...."