Fair enough. I was away and I am returning to threads for this reason.

I would suggest for you the following sequence (it takes a bit of money, though):

1. get a trendy frame if you wear glasses or sunglasses. Spend a couple of months getting used to wearing it.

2. get black yoga pants, a black tunic to go on top of it, and start buying unusual necklaces (the all-black background is forgiving and would let you experiment with different colors unless they are too dark, but you do not want dark necklaces anyway). This would be more feminine without being way different from the status quo, so it would be like a baby step. It would show your creative side - the necklace would be the focal point of the outfit and the variety of available jewelry would enable you to choose something to your liking. Finally, the outfit would be good for your figure.

3. If you do not wear earrings, get your ears pierced (one piercing in the classical style, nothing more). BLOMDAHL Swedish earring company is the best for piercing, and their website has a lookup of providers by zip code. The hole would take 6 weeks to heal, and during that time you will wear the medical grade plastic earring that was used for piercing. After 6 weeks you can start wearing other earrings. I would experiment with studs for a while - they always look classy and do not require any special hairdos. I do not know the shape of your face so I cannot say whether long earrings would be becoming to you, but studs are a no-fail option.

That is enough for 6 months of slowly growing into a more feminine style of clothing and it is an evolutionary rather than a revolutionary approach.

Best of luck.