I have done a lot of pondering on this and it may seem to some of you like this is a silly question but I will ask it anyway.
First of all, you need to park how you feel that the significant others in your life (wife/girlfriend, siblings, parents, children, co-workers, friends) will feel about this and keep the response focussed on purely the economics. I think that if you can separate that part you can give yourself a more honest answer about how you really feel about all of this.
So the question is, if you were independently wealthy, so in effect, how you were perceived would not affect your livelihood, could you conceive of the possibility of dressing 7/24? Now in this 7/24 mode it is up to you if you want to get rid of facial hair, take hormones and have facial feminization surgery (but you are not allowed to have SRS). This is about whether the femme side is deep enough to allow you to dress all the time in that mode.
To me, honestly confronting this question can have significant meaning, at least it does to me. I know that if I did not have to worry about the effect that it would have on my ability to live then in a heartbeat I would never wear a stitch of male clothing again. This is an important discovery for me because I was never sure how deeply this ran for me but I can see that part clearly now.
I am interested to see how others feel about this.