Ok so check this out:
I'm wondering if I can get away with my hair over the ears and with my new glasses for work.
My new glasses, I love them. I got them for girl mode:
It's just a wig and make-up, but I seem to be reasonably passy in public like that. A few funny looks, but mostly ignored. With my hair now starting to reach officially long, I'm thinking the wig can go in six months or so

!
I'm in a pretty conservative professional job, and deal with people all day. It's mighty tempting to push the line just a bit. I've only recently started HRT so no real changes yet, but that will come with time. My name at work is a shortened version of my full name, and it's reasonably androgynous. I insisted all the staff switch to the short version when doing client bookings and suchlike, so if I start to male-fail it will probably be fine.
So... do I push it just a bit? Or hold back? Is the glasses and hair pushing a bit too far?
Feels a bit like playing chicken!