Do clothes make the girl?

Christian Dior Dress (cc flickr user unforth)

Whether exaggerated or not, it is pretty well documented that transgendered m2f's usually dress sexier and more overtly feminine than the average woman of their age.  I assume that this has to do with the fact that until hormone treatment and/or surgery, we must rely on external indicators to validate our internal selves.  When a TG gal looks down at her body, the body hair, the genitals, the lack of hips or defined waist, the flat chest, all this combines to fight the self-image in her mind.  Now, as someone who is interested in fashion, I'm well aware that relatively flat chests and lack of pronounced hips does not make a chromosomal woman non-feminine.  But her self-image is backed up by the rest of her biology.  Even if she believes her body to be deficient, she usually doesn't see it as male!

So, what's a tg girl to do?  Overcompensate, especially at first.  Makeup tends to be caked on and often garish, and dress is often over-youthful and rather sexualized.  This does not necessarily imply a sexual component to the costume, just the influence of mass media.  This was certainly the case for me a few decades ago.  But now I'm in my early 40s.  I've been on hormones but only have little sub-A-cup breasts and no real hip/waist definition. And yet, even when I look at myself completely naked, I see the woman in me.  I'm not really happy that I see male genitalia dangling down there or that my belly is sort of poochy, but it doesn't jar me as badly as it used to.  I am much much more comfortable wearing women's clothing than men's, and I do still like dressing up a bit even when just doing chores around the house, but I also sometimes opt to wear just jeans and t-shirts with flats even when I am all alone in my house and could wear something else.  In some ways, I think of it as an evolution to thinking more like a woman than as a trans-woman.

It's sort of funny.  Over the years, I've developed a reputation (as a man) as someone who doesn't like to get dressed up.  I only put on jacket and tie if I absolutely have to.  The thing is, it wasn't about getting fancied up.  It was the overt maleness of the jacket and tie and the big clunky male dress shoes.  As a woman (at least in my mind if not in practice yet), I'd be perfectly happy to have occasion to wear nicer dresses and heels, though as I said, I'm also happy in jeans and flats these days.  I wonder if this growing comfort and knowledge of who I really am makes it more or less likely that I will be able to transition successfully.  Will there be less of a change from my current life than I expect?  Is that good or bad?