I think it could be with the right coordinate. It could also easily fall under Sweet or Country.
That’s up to you. They both have their pros and cons. With Classic you usually wouldn’t stand out quite as much because of the muted color pallet so it would be a good option if you’re particularly shy or worried about wearing Lolita in public. Sweet is more popular at the moment though and there seem to be more independent shops carrying things that work for Sweet, especially with Fairy Kei also being popular.
Either color would work fine with the pink blouse and shoes. I would personally get lavender because it’s one of my favorite colors, but either would work well in that coord. Maybe decide based on the rest of your wardrobe and which color would fit in better.
You mean like this?
I think in general they’re super adorable (I absolutely adore this one specifically because the bear is really freaking cute), but obviously there is a time and place for them and they would just look out of place with anything other than OTT Sweet.