So as a real-life avid follower of the Lolita fashion and a recent fan of Second Life (newbie! Yes, but this helps guide people to say that you can indeed buy all that I've bought on a free account), it's pretty predictable that I would be looking for the Lolita fashion in Second Life, where most of life is about fashion and shopping.
Well, if you're actively trying to avoid the "adult" areas, anyway.
It's hard to find Lolita-wear in Second Life. Mostly because the length of skirts would classify most of what the vendors consider Lolita to be in the ero-loli catagory. It seems hard for people to understand that Lolita is not about the schoolgirl uniform in an extra-short-and-tight, and more about poofy skirts and lace and frills. Still, there will be the ridiculously short skirts. It is Second Life, after all.
So here is the documentation of a Second Life Lolita who occasionally wanders off into other brands of fashion, but won't stray to your jeans and glamour shirts. There are a dozen other fashion blogs for Second Life that recommends your normal fashion-- this is one that wanders off into the Japanese and Japanese inspired clothing lines.