I decided to do this meme one point at a time because I like to ramble lengthily about everything and trying to fit all my answer in one entry would make it long as a hungry day at work. I'm probably often using photos of other lolitas to illustrate something but I promise to ask everyone's permission before I do that, just to be on the safe side.
1. Best Lolita fashion advice you've ever received?
Look good. No matter what, see that the outcome is aesthetically pleasing. It doesn't matter how many "rules" you break while at it as long as you manage to pull it off.
I cannot help it, but this is one of my favourite outfits ever, and not least because it's from the time when people still discussed what kind of shoes can or cannot be lolita. Then comes along a Lotta and is like, I have red rubber boots what say you. And I sort of went YEEEAAAHHHHH.
Despite always having been fairly strict about what looks good in lolita (my own style excluded of course; I can be wonderfully blind to my own coords sometimes) I always tend to find you cool if you're variating far away from the so called "normal style" while still looking great. Most often the key thing is to make everything about the outfit somehow explain away the other parts, like Lotta's boots that really make the outfit, while the outfit itself seems to agree with them.
It's clearly a rainy and windy autumn(?) day in Helsinki, she's wearing warm clothes and carrying a red umbrella. The gloves, the bloomers showing from under the JSK and the wind-blown look about her hair add to this (although the wind-blown part was probably just that, wind-blown and not a plan - but nevertheless it's something that usually doesn't look good in lolita but works just brilliantly here). Somehow the whole outfit seems to tell you that she's planning to hop into a puddle soon as the photo's taken. Most likely the one right next to the cameraman.
In short: while going by every rule results in good-looking coords, you'll only reach the level 9000 after you make the style your own. More about that in the next entry about style icons.