Suppose you end up walking around in the rain one day for four or six hours, which can easily happen in most European cities in winter. Would your feet still be dry and comfortable? For winter, I'd take along two pairs of shoes, and maybe this would be one of them, but I'd also have water resistant boot-style shoes too.
If they work like advertised, they should be great. But it's hard to say without extensive testing. We've had snow here the past several days, and I've been very happy for proper ankle-high boots. Are you going to be going anywhere that snow is likely?
Whatever shoe you choose, be sure that they fit you perfectly, and wear them at least a couple of days, before you leave. (I have some painfull memories, on a trip to Vienna, with a new pair od shoes ... it still hurts).
I agree, with WillTravel, that in winter, it's a must to take two pair of shoes. It can easily happen that you get soaking wet. If you have two pairs you can leave the wet pair to dry properly. (it's extra weight, but you'll appreciate them, when you need them).
Edit: I wonder if there is gonna be a real winter ... it's way to warm for the time of season, for the last couple of months (in western Europe), but no real winter, would spell: rain, rain and more rain.
The shoes in the second link look like they'll work well for winter. I don't use slip-on shoes, as I've found in the past these can sometimes "loosen up" over time; I like to have shoes solidly laced-up!
As mentioned in other posts, make sure you "break these in" for a week or two before you start travelling. If the Timberland shoes prove to be unsuitable, you'll at least have some time to get alternative footwear.
I used Rockports on my last trip and they were reasonably comfortable. However, I did have a few "foot problems" on a couple of occasions. I want to do some "fine tuning" with the local shoe expert before my next trip.
Most definitely the second ones are really good. Look wise, and comfort wise! You can wear them in winters and I would also wear them with my Carbon38 tank tops. They’re the ones I really like and going to recommend to my sister too.