Here's a little anecdote posted by Stana at Femulate:
As I waited for the elevator with six other people, a man I know joined us. I go back over 35 years with this fellow. He used to sell ham radios locally and I bought one from him eons ago. We were also officers of the same radio club back then and I even attended a Rochester, NY ham radio convention with him riding in his van with three or four others. That was way back in the mid-1970s.
Since then, I have had one other encounter with him; about ten years ago at another ham radio convention.
We both know a lot of the same people in my neck of the woods and I am not prepared to be outed to them yet, so I worried that he would recognize me.
As the elevator ride began, he asked what floor I wanted and I told him in my best feminine voice, "Mezzanine." A couple of floors down, everyone got off except he and I. He did not say a word the rest of the way, but I could feel his eyes checking me out from head to toe.
He got off one floor above my floor without saying a word. I breathed a sigh of relief because I was sure he had not figured me out. (Knowing him, if he had recognized me, he would have said something, so I guess I passed.)
And a similar one from Sandra at Tranny in Trouble:
Earlier while in guy mode at the friend’s houe where I’m staying in L.A., I talked briefly with the neighbor, an older guy who came by, and he said, “Oh, you kind of look like that lady friend who sometimes stops by – she’s tall too…” I just smiled and said something vaguely in agreement, but I don’t think he even heard me. I love when stuff like that happens! Later, I was thinking, well, maybe he’s just messing with me and obviously knows that that “lady friend” really is me dressed as a woman. But from his manner, I suspect that he just saw a resemblance but didn’t really know that, yes, that was me.
Like most people, the reality of crossdressing is probably so unfamiliar that he probably just didn’t make the connection. And that always amazes me, because like most crossdressers I always think that I don’t really look that much different in girl mode than in guy mode, though in reality most of us do look very different indeed. I have a friend who has a fairly high-profile job and every now and then he’ll have anxiety about having femme pictures on his various online profiles and he’ll be tempted to delete them. But really he looks so completely different in male mode. With the wig and makeup and clothes, it’s just so unlikely that anyone would ever recognize him. And yet so many of us, myself included, think that others will see through us just like that, without any doubt or hesitation. I do wonder, though, how long it will take for that neighbor to put two and two together, as he’s probably going to see that “lady friend” again a few more times this next week or so.
Now, I know my male self might be a special case, since my friends and acquaintances expect me to have facial hair. But what about the rest of you? Do you think your femme image is different enough from your male one that most folks wouldn't recognize you?