It's never easy making the journey from one gender to another. I am biased but I think it is one of the most difficult things a human can do.
Each of us has their own path they followed and fortunately I can share two ideas from Cyrsti's Condo readers who successfully Mtf gender transitioned.
The first comes from Paula: "I believe we go through a concentrated growing up process, those of us who transition later in life miss out on a female adolescence, we don't have benefit of either contemporaries or older women teaching us how to be women. we could observe from outside, we could watch but were never part of the sisterhood. In consequence we had a steep learning curve, I know I personally made many a teenage mistake, inappropriate hemlines, poor makeup, inappropriate personal interactions, all girls do the difference is I had to make these learning mistakes in my 50s! It can be a little embarrassing looking back on my early blog posts, the emphasis on clothes and makeup, all the photos but it is part of my process, part of my growing up, part of my history."
The second comes from Connie: "I've long held the theory that many trans women express their femininity, at least early on in their trans lives, based on what the male side of themselves find attractive. I'm not referring to autogynephilia, as this attraction is not necessarily sexual in nature. It may have something to do with separating one's female self from the male self, as well. That is, just as a trans woman may overcompensate to affect a more masculine facade while living in male-mode, she may overcompensate in her (idea of) femininity when in female-mode. That's may seem like bouncing from one caricature to the other, and, for me, was just not sustainable."
I too went through the separation phase of trying to please my former male self when it came to appearance. When I finally learned I should be dressing to blend and please other women, I finally was able to negotiate a feminine world much easier.
Thanks to you both for your comments.