I'm a ways off from comfortably fully presenting as a woman in public, but this is what I have done so far in my journey. I'm 6'3 btw and have had a belly, but have been working it off.
I have pretty much replaced all my pants and jeans with womens style/cut slacks, pants, jeans and shorts. I've not gotten any skinny style yet, rather I'm staying with straight leg or boot cuts. The trick for me was to find approximately what size range I am and I did a lot of looking on amazon and used their sizing charts which gave a good inch to number size. I wear a 33/34 waist, 34/36 inseam mens. That translates to a 14 / 16 womens tall on average. You have to look for the the tall options and read the descriptions if available., but a lot of manufactures have them, but a lot are also mail order only. From what I've seen so far, the womens talls tend to 32 to as much as a 36 inch inseam.
Im-tall-too.com is a good site for starting out, but I've bought most of my pants from amazon due to the free easy return policy on most clothes. The biggest things I had to get used to was a shorter zipper length on those pants that came with zippers and very shallow to no pockets. But I sport a nice sling shoulder bag that draws little attention as it's somewhat unisex, so the lack of pocket area is not that big of a deal, but I still had to get used to it. In face it's helped me break one big "man" habit of standing around with my hands in my pockets.
Also socks are socks, but there are some which are distinctly more girly. I really like the ones with the half fold. I did that with my tube socks and have recently added several pair of regular womens socks to my wardrobe.
I'm still having problems with the tops area. Most have narrower shoulder areas, both width and depth and are really tight, and in amost all cases long sleeves aren't long enough. I'm not giving up, just taking longer. I have taken to wearing sleeveless tops of various styles around the house though.
In the shoes I can't help a whole lot. I'm lucky in that I wear a 10mens and that's about an 11.5 to 12 (mostly 12) on womens and have a lot of choices. I've found a real nice pair of clarks slipon loafers in neutral leather (not patent) that looks nicely femenine, but not overly so and so don't draw too much direct attention while out. The heels are a very slight wedge of about 1.5 inches that don't push my height too much, but I know I've got them on.
I wear the pants and shoes out all the time and it's helped me get more confidence.
I hope some of this helps and good luck and have fun shopping.
-Becka
