There's a lovely little vintage clothing store down the road where my wife and I have been going regularly to augment my (and her) wardrobe. I am not yet out locally, so I go in boy mode. I have tried to be discrete when going to the change rooms to try on skirts and tops, so as not to freak out other customers.
But I am pretty sure that one of the owners has noticed me a few times. She's a lovely elderly lady, and we figured that some day soon I should come out to her.
So, today, she was on duty. After browsing the racks for a while, we chatted with her for a while. Then, at my wife's urging, I told her, "When I am looking at the clothes, I am shopping for myself." It took her a second or two to realize what I meant, but then she was totally sweet about it. She touched my arm and asked what styles I preferred. She wanted to know my new name and whether I had started HRT yet. Just a total dear.

It is amazing how much lighter I feel any time I come out to someone new! So far I have had only good experiences.