This is a rough question;
But I will try, at least it is my 2 cents worth.
Today, most women do not dress very fem, unless it is for work or a special occasion.
Just look around at say the grocery store. They all wear jeans and a top, and flats or
tennis shoes.
Even my wife, is in pants 90% of the time. Only wears a skirt for a church or other
special occasion. She says that she is most comfortable that way. She gives me the
raspberries when she see me in a dress and hose just to hang around the house.
Now getting back to your question; Dress the way you feel most comfortable in.
If you like a dress or a skirt, wear it. But only do it for you, not to impress anyone.
You said that some of your family is indifferent about your dressing, so dress down
around them. Seeing you dressed to the nines might put them in a state of shock.
Remember, society is still in the dark on our dressing, so we must adapt to a less
tolerant society than a liberal one. Some day our Ship will come in, but for now I
guess moderation is the word for the day.
Rader