A few weeks ago I was out shopping as Claire. I was looking for a particular product in one store but it was out of stock. I got talking with the owner (it's a small local business) who offered to order the product for me. She texted me a few days later to let me know they had received their shipment. A week or so went by without getting a chance to pick up my order. Yesterday I was in the neighborhood in male mode, but I stopped in anyway.
When I told the owner I was there to pick up my order, she gave me a puzzled look. I told her it was for Claire. She kept looking at me quizzically, then made the connection. She gushed on for several minutes how well I had done my makeup and outfit, and the had I not told her, she would have never made the connection i was the same person. I was quite pleased that this woman had been so complimentary of my presentation as Claire.
When I first considered stepping out in public, I read on a website for a CD support group that people will likely see you as a man in a dress but with the wig, makeup and outfit it is unlikely someone will see YOU in a dress. That interaction affirmed the website observation.