At 6ft tall, ugly as sin, almost as bald as a cue ball, super-sized super orbital ridges, big feet, frog hands, and deeper then the average males voice, I experimented with transitioning twice in my past, both times utter fails. A lot due to attitude. I never allowed my self to put those "Some Guy" in a dress thoughts in the rubbish bin where they belong.
Almost 30 years latter about the positive physical change is being an inch shorter. Emotionally a lot has changed. However, I also put in the extra time to have as unambiguous female presentation as possible. Loving girlie-girl is a plus. I also do casual like jeans, when more appropriate.
Perhaps it's luck, but I haven't been mis-gendered yet nor had any of the confrontations I did 30 years ago. Today when I do get those lingering a tad too long stares I chalk them up to looking pretty good for an old bat rather then the immediate going negative response I had. I am sure the shear joy of being out in the real world as the real me has a lot to do with looking at the positive side.