I think you're very smart to do a gradual change. When someone who normally presents as very male looking suddenly switches with the whole works it can seem artificial to others (read "impersonator"). The gradual approach allows you to get used to the transition. In fact, some of us, like me and, I believe, Barbie (above), choose to not make a full transition, but are simply more comfortable with a feminine visual identity (but not a physiological one).
I find there are fewer hard social boundaries regarding gender than one might at first think. You can, without definitely presenting as female, wear most hairstyles, a great deal of women's wear, jewelry, and less-noticeable makeup (like cover-up, mascara, etc.).
The only hard line crossers seem to be skirts, dresses, high heels, sheer hosery, leggings, bras (and fillers), obvious makeup (eyeliner, eye shadow, lipstick), and very feminine hairstyles such as updos.
I never try for an "andro" look with any of those items. Once you slip on that skirt, you really need to finish things up. But other than that, the gradual approach works well and is a pretty good idea, I think.
Lyric