I got your back bro.
Top - Polo Desert Boot - those are in that shape after, no shit, 11 years of nearly daily use. For years, they were nearly the only thing I wore in business casual settings. Now that I'm back at school, it's Nikes most of the time, and these boots when winter comes and the jeans replace cargo shorts. They may indeed last forever. Soles are Goodyear welted. They retailed for $225 back when I bought them [just by chance for very VERY much less], and I saw a pair at Macys a year or so ago selling for $375.
Bottom - Johnston and Murphy [I think that they call it the Cumberland nowadays]. Only 4-5 years old, but also not showing wear much at all [outside of laces, oh and the Polo laces are ALSO original]. Very VERY comfortable. Probably most comfortable I own outside my Bacco Buccis.