I am still, very much so, having difficulty in sorting out how far to go(?). In other words my TG Group, Therapist, and Wife ALL beat me over the head about obsessing over a totally unknown and uncontrollable future. (I'll spare you the "Who made you God" portion). "What If'ing" things to death is my stock in trade and pays me very well. I am just piss poor at applying that talent to myself.
HRT has been a real life changer/saver for me. I know I need it for my emotional health. The rest is gravy. After a year or so I developed a fairly good A to maybe B cup. (A lot depends on the bra thanks to vanity sizing). I primarily present as male with no issues. (OK, the wife does throw out the occasional bouncing boobie comment.) Being a former fatty, in male mode I NEVER wear anything form fitting. In female mode my bra of choice is a VS super maximizing one.
Clothing is simple. You likely have a vague sense of what look you like. Whether or not it works for you is another issue. My favorite places to shop are thrift stores. For a few bucks you get to experiment. Department stores you can generally find some great sales. You have a choice of either buying in multiple sizes and return later (drain on cash flow and time). Or, a technique I used for male mode shopping, grab an armload of stuff you want to try on, top it off with a pair of super extra large pants or top from the men's department and head for the fitting room.
I found that after all the hard self-improvement work I did how I looked became secondary to actually being out in the real world as the real me. Eventually I achieved my life long dream of being seen as and accepted as a woman. If you ever have doubts about how good you look, follow this advice. The next time you are in a Wallymart or in the grocery store checkout line, look around at ALL the other normal everyday women in line with you. FAR from what you will see on the cover of Vogue, when you eventually get there. Just plain ole women being women.
Between me liking girlie-girl and some lack of self confidence I generally try to present a clearly unambiguous female image. Living in rural WV in a land of 5'4" 250 lb jean wearing women, I have had no problems aside from the occassional seems like too long of a look, even stare. Since I cannot know what is in their head I tell myself it is simply because this 6ft tall 145 lb fairly nicely dressed woman looks good. It sure beats beating myself up with the alternative.
SO's are always a wildcard. Initial reactions may only be fleeting. Like all things in life, expect change. My wife was FAR from thrilled when I dropped the T-Bomb on her 6 years ago. And she knew I was a CD, saw me dress at home, and was even told about my "Experiments" with transitioning. Well, that was 30+ years ago. THings change. I gave trying to be a "Normal" guy (within limits) my best shot. Over time she began noticing how me coming to know and accept myself made me a far better person overall. Yeah, some things like seeing boobs on me along with my naturally big hips bother her some. But given the trade off between the old miserable, soulless, >-bleeped-< me, or the realer me; she prefers the realistic version.
Long term is still unknown. I cannot ask her to stay by my side anymore than she can ask me to stop all that I have doing. Neither of us want to stand in the way of the others happiness. We just play it by ear while keeping up our honest open discussions, hopefully not reaching that dreaded TMI point. Considering the totally dysfunctional families we both come from, we are doing stellar work keeping things together.
Finding peace is not a either this or that choice. If you only allow yourself to think in terms of Male / Female you close yourself off from thinking or seeing that there are an infinite number of ways to be happy without resorting to binary choices. Every decision you make in life involves a cost. Only you can decide if all the trade offs, or cost, is worth the chance of achieving what you want or need, TODAY. What works for you today may not tomorrow. Again Binary thinking locks you into few all or nothing choices. Not a mindset I want to live. I know it didn't work at one end of the spectrum, likely will not for the other. Each day I am growing and learning a little more about myself and the world around me. What worked yesterday may not today. Hopefully I have a Plan B, or a new tool in reserve, to carry me through the next potential change