Fun topic and discussion! Thanks for starting this, Lisa.
I'm in Group Three -- the "no sneakers in school" camp. I was singularly unathletic. (Which is hilarious when you consider that I grew up-- eventually -- to work for a fitness company for a while and became something of an expert on different types of exercise and exercise nutrition!)
I was similarly incapable (or uninterested) in math and I was scared of the artsy types (even though I secretly longed to be one). That left me on the fringes of everything, pretty much. What did I wear? Mostly platforms of some kind or another.
I did wear Docs in my college years, but the more refined monk-strap kind. Loved them at the time...
I do admit to have tried Converse on a few times, but they did not fit me or feel right -- I was never good in a completely flat unpadded shoe. The first ones I owned were my beloved Hi-Ness (with the little wedge) and I adored those and felt perfectly happy in them until they died.
Now I love my Eccos, which are basically comfort shoes, but that is okay with me. I am seriously considering adding a pair of the high tops this fall...or a red pair of the Soft 7s or 8s....