[asark]

With you on that, been really happy wearing nicer leather "work"-style boots. They look good, they wear great (after the first couple foot-destroying weeks), they last for-friggin'-ever, and beating them up doesn't really hurt their aesthetic, so far as that goes. I've gone the Redwing Heritage route, getting one pair at a store and using that sizing to buy a couple pairs of seconds in other styles at ~40% off retail for firsts.

I've also become a loafers fan. In US fashion, at least, a good pair of black or dark brown loafers can be worn all the way up to business-formal, to weddings, funerals, et c., but also dressed down to business- or smart-casual, and if they get beat up they just become toss-on-and-go shoes for any occasion, even if it's just mowing the lawn. Again, they last a good long time if they're US- or European-made. I don't think either beats cheap sneakers for price over a lifetime, but then you get whatever benefit a nicer look and a little more formality-range gets you from going for well-crafted leather, and they aren't so much more expensive considering that and how long they last. Sure $200+ for a pair of shoes is a bit of a shock at first, but when they're in your rotation for 10-20 years it seems less crazy.