I can't recall the first time I put on an item of womenswear. I was probably in my early teens and I am pretty sure that up to that point it had not occurred to me. No recollection why I did or of why I continued. I do remember I would initially only put on outerwear. My mother kept her slips and some other underwear in some drawers in my bedroom but I never even looked at them - at that stage I thought underwear would put me in some sort of gender limbo. I think the dressing only expanded beyond occasional trying on of dresses and shoes when I went away to University. I could have clothes of my own and dress without fear of someone walking into my bedroom and seeing me in a dress. At some stage the dresses were joined by underwear and then accessories. My boobs were just rolled up knickers.
I bought lots of clothes but this was about quantity not quality. I realised some clothes suited me more than others but only after wearing them and at this stage I was scared to try anything on in a shop.
The turning point came when I decided I really wanted to know what clothes were best for me. I found a colour and style company that seemed head and shoulders above the others and when I was in London, far from home, I made an appointment and went along in a skirt, blouse and silk jacket. The consultation was pricey but without getting a single new garment, it was the most sensible expenditure I ever made on clothes. These two ladies literally changed my life. I was so impressed I went back and got a male style consultation too.
It turned out my best colours were not the ones I thought, and they guided me to garment styles that were much more suitable for me than the ones I had been wearing. It turned out I needed expensive, classical clothes and leather shoes (a particular style of court) and they taught me make up and what colour and style of wig to go for.
I now have a vast collection of skirts, dresses, tops and shoes - almost all othem in colours and styles that really work for me. I confess I lapse occasionally and buy a dress for fun or because I love it as a dress. One of the rules is NEVER wear black next to your face (it is suited to only one colour season). I went to a refresher a few years ago with a different consultant in the same group, and I had to bring along ten dresses I loved. One of them was black. The consultant took one look at it and said "I don't care if it is black - that dress is to die for".
I only go out dressed occasionally. I would have been going out today but the weather forecast is horrific to the extent that I might not get home tonight if I went where I had intended. I often meet up with a very well dressed woman friend, about 50% of the time I dress as a woman when we meet. I have achieved all the challenges I set myself when dressed - bra fittings, restaurants, stays in hotels, beauticians, dressmakers (including being pinned for dress alterations), bars, visits to stately homes, doing the weekly shop, public transport, etc. There are no new challenges, so I have reached a happy plateau. I miss having a partner but am not actively seeking a new one.
I have long ago accepted that I like to look like a woman and when I go out in a dress, act like one, but at no point do I imagine myself to be one. It is acting. I love the outfits and how I look in them - to myself and others. Women praise me for my outfits. I am out only to a few friends. My only concern is that I spend far too much money on new clothes I don't need - and I long ago ran out of wardrobe space.
So I set out to be the best dressed I can be in womenswear and I achieved it. I own lots of lovely women's clothes (I know the Eddie Izzard thing, but I use it for convenience) and I wear them to my heart's content. I even have a lovely (and well dressed) woman friend I can share this with though we are not an item. I have the sort of life in a dress I always wished for and it is a good place to be. It has evolved through seeking professional advice from women who know what they are doing - the same professionals women go to when they want to achieve a fantastic look. Going to professional colour and style consultants is possibly even more life transforming for us than it is for GGs.
