Unlike fussy metrosexuals, regular guys do not worry overly much about their appearance (unless at work, on the golf course, or at the club). Yes, regular grooming habits do seem necessary, as do clean if not ironed clothing.
This post, however, is about so-called "old man walking shoes." In NYC, or when travelling in Europe and parts beyond where you end up walking many cement or asphalt miles in a day, it makes sense to swallow one's vanity and to invest in some seriously comfortable walkin' shoes. I don't mean huntin' and hikin' boots.
I have worn out one pair of expensive Mephistos, but for comfort, support, and general ugliness, these New Balance walking shoes are the best. Cheap, too, and ugly enough in black to exceed the criteria for "old men's walking shoes." (If you get them in white, you look like you should be pattering around a nursing home.)
And consider this: If you are a cool, interesting, streetable man who is good at sparkling conversation, oblique flirtation, and snappy repartee - as I am - only a moron would hold the provenance of your shoes against you.
(This does not, obviously, apply to women and shoes, which is a subject of deep mystery to all.)