Help picking out chukkas for winter!

I've only got personal experience with the Brecon, but let me say this: If your Canadian winters are anything like our Swedish ones, I'd say that neither one of these shoes are a good choice. If you live in an area where you can be 100 % certain that there won't be any snow, ice or wet ground then go ahead and pick your personal favourite. If the above does not apply to where you live I'd frankly opt for warm and properly insulated boots or shoes on your way to the office and leaving a few pair of nice shoes at the office to swap for once you arrive.

If you are going to buy one of the chukkas mentioned in your post for winter wear with snow and ice, consider this: the double leather sole of the Alden combined with ice could be a death trap if you're unlucky. The dainite of the Brecon works well on snow from my experience, but I've almost fallen on my ass several times walking on wet coblestones. I would not like to wear them while walking on ice. The sole of the Cole Haan does have rubber inserts, but I've no clue as to how much that'd help. They're not exactly the most attractive boots of all time in any case.