My first time wearing Lolita in public was at an outdoor meetup at an arts festival. It wasn't too out of the ordinary to see things like crazy fashions and what not. There was a big group of us so I felt comfortable. I got some stares, but otherwise everyone had really positive reactions.
I've not yet encountered any downright negative reactions in Lolita yet, as I don't wear it in public very much, and if I do, I try to tone it down and mature it up as much as possible so I don't look too horribly out of place.
herp to the derp.