The first time I wore lolita out in public was to a small cosplay picnic at a park. There weren't many people there so no one really paid me any mind. We wandered into the nearby mall afterwards and we got some stares, but I can't say if it was because of me, my cosplaying friend (who was half in cosplay - she was worried about walking around there in bootyshorts so she had my petti on), or the both of us. Nevertheless, it was a lot more tame than I thought it would be.
The first time I wore one of my own skirts I made out in public was at the last convention - Fan Expo. The day I decided to wear it happened to be the same day as the organized lolita photo op, so there were a ton of girls in lolita who would just stare at me as I walked past. I remember there was this one time where I was going back to the hotel when a girl in a JSK walked by and just started to stare me down without saying anything, pretty much until she walked past. I'm not good with something like that so I started looking down instead. (Just curious : Is there a solution to this?) No one said anything directly to me about my skirt during the convention (which, to me, is a good thing), except for my friend, who was one of the organisers who tried to convince me to join the photo op.