Copy/pasta'd from another place:
For about 3 or 4 years now, I've been swearing by Common Projects. They're expensive, and quite possibly too minimalist (read: boring) for some, but I've a) never paid full price, and b) gotten my money's worth, as my oldest pair (the first ones below) have gone through 4 Canadian winters as my primary shoe and other than a replacement pair of laces from CP themselves, for free, I've never had a problem.
Dark Gray Midtop
Patent White Midtop
Court Shoe Low
The courts were my favourite sockless summer shoe, ever, but after two summers of being treated like that, they're semi-retired. Should've bought a second pair :-/
Other than that, I stick to Converse and the occasional pair of Vans, but lately I've had the urge to get a pair of ridiculous Dunks. And a new pair of Sperry's now that it's finally consistently warm up here.
...
This is now the fifth winter for those gray suckers, and they're still going strong. Just had the lace on the patents snap last month, sadly. I've got some massive clunky winter boots for when there's a ton of snow out there, but my other main rotations are a beat up pair of canvas high Chucks, some Cole Haan oxfords, and these Rachel Comeys:
I've got a pair of Raf Simons metallic high tops that are ridiculous, and I never wear them thanks to a problem with the foil wrap, but I keep them for the design; they're a favourite.