I'm just back from Ireland and the saving grace of my trip was these boots. They are stylish leather boots that come in ankle and midcalf heights. (I had the former, in black.) In Ireland, there were short periods of rain (sometimes, downpours) every day and my feet stayed dry. They're also comfortable to walk I'm, including on inclines, and they have a lugged sole.
I got mine from Amazon, though other retailers likely have them. I didn't need a breaking-in period asnthey fit perfectly right out of the box (and that's not typical for me). If you're looking for a boot that's comfy for daytime and looks good for going out to dinner, these definitely fit the bill.