Baggins is cool, their store is fun to check out everytime I'm in Victoria. Haven't actually bought anything there yet, but eventually I might. Those Sailor Jerrys are pretty cool.
Nice to see you guys rockin' the mod boots. Makes me think of the Beatles, but I guess it fits Bond too.
I managed to find a nice pair of monochrome black Chuck Taylor combat-esque boots that function as my warm-weather rainboots at Zellers of all places. I think they were $30 when the final clearances were happening. Must've been old stock from The Bay or something, but man was that a sweet deal. I still get people asking about them fairly regularly. Like these, but with round laces:
For preppy-yet-classy, say a casual date night or hanging out with friends, I have a nice pair of Sperry Topsider chukkas, best of both worlds! I also got them on mega-clearance the same day as the Chuck boots.
For daily casual wear I think I prefer Vans over Chucks these days. The big rubber toe on regular Chucks make my feet look silly. All-leather ones are pretty good though. My regular day-to-day warm weather shoes are classic checkerboard Vans in navy & burgundy. Sadly they've probably only got a few months left in them, and I haven't seen that colorway since I picked them up at Winners a couple years back...
For dressy occasions, I'm more of a wingtip type of guy. Nice dark brown brogue with slim sole is where it's at. Of course, it's not the dressiest of shoes, so for truly formal occasions I prefer a black leather cap-toe oxford. I still have to find myself a quality pair of both.
I often go for classic with a twist. Interesting materials, atypical colors, etc.
Shoes, man. Almost as awesome as robots.