Euhm the most i can offer is try to do "practice runs " with a friend or in my case my Sister with a skirt on.
That way you get a feeling how it is,and with someone by your side the fear should not be to great to handle.
Second,decent simple make-up helped a lot during my first trial out my Sister helped me with my make-up something really simple: Vichy liftactif eye cream,moisturizer,colored natural BB cream evening out on the area around the cheeks and eyes and nose with special brushe,and light eye shadow. This helped me out huge and this little make-up routine is simple and effective enough to use daily. ( god i love colored BB cream ).
I did practice runs twice second time was with my Sister and a friend (female),this week i enough confidence to go out in grocery shopping in a pink skirt with matching Sandals and the make-up on like my Sister teached me. No stares.
Picture of me first time with my Sister ;
You can do this !
I suffer from Alocepia hence the short hair but i am no longer let it impede me to wear nice skirts. And i am slowly regaining my hair still have some bald spots on my scalp but my hair is slowly getting back this picture is recent 6 months H.R.T in and i was bald on top in the beginning .... So i choose androgynous look to to start with.