The man is in his 50s and should wear whatever he wants.
Honestly, I think entirely discounting shoes just because they are made for a fashion brand is narrow minded. I mean, I've never seen a Prada shoe I like, but I'm sure not all of them are ugly junk.
I own a couple of pairs of Gucci horsebit loafers and a pair of Ferragamo bit loafers I enjoy wearing. They may be fashion brands but I feel they are beautiful, and their quality is worth the cost. If this fellow feels the same about his Pradas, then he's getting his money's worth.
I disagree with most of that.
I am in my '50s and I certainly wear what I want. I undoubtedly push the boundaries of the very conservative envelope that defines the norms of my profession because I want to and because I can. But there is no reason to abandon good taste upon attaining that age, as the OP has quite proudly declared. And I would not encourage others to abandon good taste at any point in their lives or for any reason.
His obvious troll post is fueled by two provocative and wholly misinformed narratives: 1) that traditional high quality men's footwear is desperately boring, and 2) that Prada footwear allows him to break free of the dull and uninspired aesthetics on offer by traditional manufacturers at no deficit save a purely notional reduction in ultimate durability.
The first, I hope is such obvious nonsense that need not comment further. Certainly the mountain of evidence to the contrary, as posted by several members of this forum, should obviate the need to dignify his claim with further discussion. Note that the OP has neither commented on those photos posted, nor shared with us his supposedly vast array of high quality but utterly boring Edward Green and Crockett and Jones footwear.
As to the second, well, just look at the pair he has selected: hardly dynamic cutting edge styling. Not any kind of an "I just gotta be me!" aesthetic departure from traditional norms. I can think of a half dozen footwear choices that present more of a statement of individuality, while still offering vastly superior quality. So it has a high polish. Wow. Take a walk on the wild side. For THAT he's going to declare that he's done with traditional brands and flying the PRADA flag full time? Please.
You said it yourself: "
I've never seen a Prada shoe that I like...." This is an observation which I believe that most with a modicum of good taste would embrace as their own. This begs the question: what possible benefit could there be to searching for the exception to that rule within the confines of a brand that is literally defined by shilling overpriced junk to those cognizant of brand and ignorant of all else? Why would one wish to promote here - on a forum quite literally dedicated to the preservation of sartorial good taste - the acceptance of a brand which proudly promotes footwear so astonishingly ugly as to be laugh-out-loud comical?
Answer = classic troll post.