I think we are missing the boat here, if you pardon the pun. We are looking at Topsiders as form, rather than function. They are one of the all-time great summer shoes for hanging out at a lake, on a boat, running to the store real quick for a gallon of milk, etc. Great not for how they look, but for what they offer. Easy wear, slip on slip off, doesn't matter if you get drunk while fishing on the dock and fall in the lake wearing them. For me, they are not a fashion statement and never were.
I think they can very much be fashion statements. 80s prep is all about the Topsiders and a polo.