I took much the same approach as MariaMx, starting with longer hair, then clear polish on my nails, then pale pink polish, then neater eyebrows, then a switch to ladies jeans, etc, etc, all over a period 6 to 12 months.
My biggest boost was when I realized that I no longer cared what other people thought about me and that for most people, most of the time, I would never ever see them again. Their opinion of me was irrelevant so I could dress as I please. Once I had that figured out it all started getting easier and dark nail polish made an appearance. So did make up. Ear piercing was soooo good as was starting to wear a bracelet and a necklace. Perfume is a nuisance until you find your own scent that suits you and then it is heavenly.
I love feeling lipstick on my lips and it helps moisturise them because I did not appreciate how much hormones would dry my skin out. Male skin is a lot more oily and sweaty than female skin. Moisturiser and exfoliating can make a huge difference to your skin quality as can laser hair removal or electrolysis.
Now, about 18 months after starting with painted toe nails I am fulltime and comfortable with it.
Just push a little bit each week/month and you get there eventually. It is not a race after all.....