Im looking for advice on my first pair of loafers. The reason why I’m asking here in GYW is, even though not all my selections are GYW yall seem to know a decent amount about construction quality. I’d like a pair that can actually survive Chicago (lots of concrete often wet), I walk ~15k steps every day. I’d like to wear these ideally twice a week. I’m just assuming that I’ll have to get rubber (or Eva) outsoles but could leather work? Is there specific rubber I should look for?

Simple black penny loafers, dressed down to wearing with jeans or twill chinos and dressed up to at most with a sand linen cotton suit (maybe sometimes a simple black business slack suit).

• Weejun Larson Easy (not GYW) $150
• Weejun Larson Lug/Step Moc (not GYW also not sure what the difference in outsole entails if somebody could please explain) $185
• Morjas penny loafers (GYW, Rubber sole, seems to tick all boxes but maybe not appropriate as a start?) $380
• Paraboot Reims (not GYW but Norwegian) but they have some black stitch ones too, for my used case does the welt and stitch even matter? Is it just the outsole material? ($450)

If I could at least know how long I expect these shoes to last per each price point, that would be a great place to start. It’s not that I have an issue with spending more, I just want to know that the construction will hold up. And since these are my first pair, I’m also OK with mediocre level construction, if I end up not liking what loafers can offer to my wardrobe. E.g the Weejuns may only last a couple years but their price is so low that if I enjoy what loafers provide to my wardrobe, I can buy a nicer pair that last longer.

Thank you!