Today I have been out twice - to a business meeting and then a social meet in the local pub. Both times I went out in knee-length boots, jeggings, t-top and a light fleece made by welshgirl (nice flare at the hips to simulate "hips").
At the meeting - in a cafe - I had a nice look from the waitress, and my colleagues were as usual fine, the new business person we met looked, noticed, said nothing, but kept admiring, she liked my dressing (bear in mind this is no wig, no make-up, just man in women's clothing), and invited me to go shopping with her after, which we did, even a shop where we had to take our boots off, and it was really evident - the assistant appeared to notice nothing/no reaction/no nothing, nor at the next shop. On the High St, again, lots of people, no-one really noticing.
In the pub also, the landlord appeared to notice nothing, a rowdy group of guys also nothing. it all seemed easy and uneventful, but for me, well it's settled any nerves about the man-in-a-dress issue, and I'm ready to roll-out the lifestyle. This is me. :-)