If it's any help, I did not leave the house in girl mode until I started feeling comfortable. Let's face it, I was scared sh*tless at first because I thought I looked like a shaven ape in a dress. I took "baby steps", which helped me a lot with building confidence, which IMO is the key.
My therapist basically double dog dared me to come to therapy as Jill. I wasn't even close to ready. I was on hormones for only one month.
The next day was first time I even ventured out the front door, and it was unexpected. My wife came home with a lot of groceries and I didn't even know that she was at the store. I was wearing a cute skirt and full makeup and helped her get them out of the car. Nothing bad happened to me.
The next week, I got in the car and was driven around West Hollywood. Nothing bad happened. Nobody even noticed me.
The following week, I took antianxitey meds and went to therapy as me. I had yet to step out properly, but my therapist's office was in the gayborhood anyway. Nobody even batted an eye.
The next weekend I went out of town wearing a dress. I had drinks at the hotel bar. I was pointed at, laughed at and stared at. Well, at least I got that over with! It wasn't really my presentation that outed me, it was my demeanor. I was nervous and it showed. I worked on that immediately. The next night I used the ladies' room for the first time. No big deal.
For my next adventure a few days later, I went to a restaurant in town that I often go to, but am not well-known there. I overheard someone at the next table say, "Is that a guy or a girl?" The other guy asked, "Which one?" The third guy said, "Who cares?" Hey, my first "pass"!
I started going out at night to work on it, but went out in boy mode during the day.
One day, I went to the grocery store and noticed my protruding nipples. I felt very ridiculous trying to "butch" it up that day, and it turned out that I never went out in boy mode ever again. I was on E for just two months. It was not my intent to consciously start RLE, it just sort of happened organically. I spent an entire week in girl mode going everywhere I normally do, then I went to Las Vegas. I packed boy clothes "just in case", but never wore them. I passed fine. The only weird stares and looks I got were when I kissed my wife. Apparently nobody noticed I was trans, they just saw "icky lesbians". I decided that weekend that I was going to make it permanent and started purging my guy clothes when I got home. My fears, as it turned out, were mostly unfounded. Once I squashed my fears of the unknown, I was finally free to be me.
I formulated a plan and came out to the world two weeks later.
