I’ll only comment on wigs, feminine facial features and clothes sizing…
I have a couple of wigs, but I don’t wear them often. The primary reason is that I cannot put them on by myself due to arthritic shoulders and elbows. I have to have my wife do it for me. That isn’t a problem for her, but sometimes she is away or occupied with other things. My solution is wearing hats. That started several years ago. I am dressed 80% to 90% of the time when I leave my house. I wear a wig maybe 2 or 3 times a year. The other issue is that I live in the SoCal desert where summers have days that are 120F+. Anyway, the choice of wigs is more related to how the cut compliments your facial shape, size and features. It isn’t really any different for crossdressers/trans women compared to those assigned female at birth in this respect. However, one thing that does come into play is the size of the head. Some wigs are done in larger sizes to fit larger heads. Search for web sites for wig vendors and some have advice on finding the right one.
Other than surgery there isn’t much you can do to change facial features. However, you can emphasize or de-emphasize features with various makeup techniques. Visit makeup counters/stores and consult with professionals. Drug store folks will not have that expertise.
As far as clothes sizing goes, first take your measurements. You need a cloth measuring tape for this. Many web sites for department stores and clothing stores with have charts that show you where to measure. The pages for individual items will have a link that will take you to a size chart. That is where you will compare your measurements to the measurements for the dress, pants, etc. The thing to remember is that there is not much size consistency between manufacturers and often within the same manufacturer. There is no such thing as standard sizing. I have pants in size 14 and 16, for example. I have 5 dresses by Sharagano that are essentially the same style and fit, yet the tag sizes are 14, 16 and 18. Also, dresses may be designed for a tradition fit, oversize, body conforming, etc. Even though the numeric size may be the same, they may all fit very differently. If you cannot try on an item, pay close attention to the size chart information. What I have found is that there is only ONE THING that I buy sight unseen. That is Amanda jeans by Gloria Vanderbilt. Their size 14 in that style has not wavered. Now, one final thing to be decided is bust size. When you take your chest measurement, that is the band size. The bust measurement takes how the breast projects into consideration. A good site for information on bras and how to measure is herroom.com.