While they're technically not chucks, vans authentics are within the same canvas category. They are my favorite and most worn shoe because they're so versatile. I have three pairs in white, blue, and brown and wear them just about everywhere, even to work on occasion. The white pair are beginning to get just the right amount of dirty. Perfect for going to shows. I just wish the winter hadn't been so harsh this year, or they would have been worn more.
I just recently started wearing Sperrys as my "work" shoe, and they've been great so far. They go well with chinos, but I'm reluctant to wear them with my APC NS's. Perhaps when the warmer spring days come around, I'll cuff the jawns a bit to show a little ankle.
As far as desert boots are concerned, I'm still waiting to buy a pair. They'll probably be my next splurge on a new shoe purchase.
Red Wings are a bit too pricey at the moment. Plus, winter will soon be behind us. I'll wait until next fall to pull the trigger on a pair of those.