I purchased the shoes I'm replacing in 1992. Blucher/Derby style, plain toe, welted rubber sole, probably calfskin. A fairly informal shoe that could move between an evening in a blazer and the sidelines of a soccer field. I have replaced the sole twice and recrafted the leather twice; the lining has come loose, stitching is pulling away from the leather, so I think it's time to replace them. No idea what model these are, but they look a little like the current AE Chicago or Alpine.
There was a time when I would have considered another pair of Allen Edmonds or maybe Johnston & Murphy, but in my opinion, those brands have seen better days. Allen Edmonds still makes a solid shell cordovan shoe, but i like Alden's shell offerings more, and i need something more casual.
Current options under consideration to replace them: Alden plain toe bluchers, models 941C, 9431S, 9432S. they're options, but $500-$600 seems like a lot of money for a casual shoe, even if they might also last 30 years. I'm also looking at Rancourt's Camden Derby. I have been happy the past several years with other shoes from Alden and Rancourt.
Other suggestions welcome.
