I came out to myself, and about a month later I didn't recognize my face and body as "me."
Once I'd decided to begin the process, I started with "no more haircuts", earrings, and nail polish. These things took about 2 months to complete, and toward the end of that I started wearing Capri's and women's sandals outdoors. For shirts, I either wore "girlie" t-shirts (ie, fairie print, pegasus, etc) or regular shirts I'd got from the women's section at thrift stores.
I wore that style for many months, during which time I was taking herbs and doing the process to get on hrt, which happened about a year after I came out to myself. 6 months later my ex and I separated and within a day I'd chucked all my man-clothes and started introducing myself as Beth.
But...everyone's journey is different. Do things when you feel ready for them; you'll know when that is. And take it slow, or at least deliberate in your choices. Enjoy the process, savor each step of the way!