You’re tripping me up with the need for them to look nice and being a luxury dealership. Otherwise I was thinking like a nice pair of leather boots like Timberland which could be waterproof. They can look okay with khaki pants or slacks but I don’t know if they would work for you in this scenario.
I just googled waterproof dress shoes. I came up with these but can’t swear they are waterproof. I don’t know if that’s super important, but I’m thinking that waterproof ones would tend to be warm. These would definitely work well with khakis.
Maybe Google insulated dress shoes.
For comfort you probably don’t want like a straight-up office dress shoe. Especially being in a cold climate you don’t want anything leather sold because it’ll just get torn up.
Brand, style, and heel height are all going to matter. So you may find you have more room and a round toe or almond toe or like more of a sandal. And therefore you might have to go down and have size. But the bottom line is pretty much just have to try on every shoe you wear to make sure it’s okay.
I like the idea of properly measuring your foot. Make sure you don’t have a wide foot. Which is fine if you do because there are wide with shoes available. Which is rule that out as an issue.
With any kind of shoe I recommend either trying them on in a store or if you’re ordering online make sure it’s a website that has free returns. And that way you can try them on and maybe walk around on them on carpet before deciding to keep them.
Going to add this. Even within the same brand sometimes different shoes will fit differently. So even if you find a pair and they’re perfect and you think you’ll just order some more from that brand, you still need to plan on trying them on and making sure they fit before you keep them.
One more thing. For shoes you already own you can get these inserts from Dr Scholl’s to go under the ball of your foot. They’re kind of round and 2 in by 2 in. Really their purpose is to provide you a little extra cushion. But what they also do is they actually push your foot back a little bit. So if you already own a pair of shoes that are slipping you could try putting these in there and they may tighten up the fit a little bit.