My 2¢:
Try it out and see.
I started off slow. Basically getting out of the house, the first stop for going out as me was my therapist. Well, not entirely. I wore a feminine top and a pair of men's skinny jeans. It probably looked ridiculous but nobody said a word. Probably helped that I was walking around Chelsea, NYC.
Bolder steps were when I completed the outfit and started wearing women's jeans. Went to my new therapist dressed up that way. I also bought a winter jacket and wore that. That was the tipping point. Without makeup I was getting "miss" and "ma'am" with doors held open and the like. I still didn't go FT yet and I'm not going to until summer. Clothes are just one part of it. When I shaped the brows that kind of sealed the deal.
Now I go out all the time as me. I don't go to work fully as me but I push it, partially covered by sweaters and outerwear.
The reason for this is twofold.
One, work wants a hard date more or less. I want my name and gender marker change before I do that. I also want to do our taxes before I change my name.
Two, I plan to do this over summer because I will likely be going for VFS then, and the kids are off school so I won't have any questions if I just show up as a woman one day in the middle of the school year.
But... The best made plans often change. If I can get my voice somewhat passable, I will probably go FT at work sooner. School remains the only obstacle, but I can deal with that somewhat by partially covering up.
This is why starting transition over winter is a good thing.
I also need to get rid of the square man glasses and do my makeup properly, both of which depend on $ so I'm trying to iron that out first.