I am probably older than most people on this thread. It occurs to me that I don't need/want my shoes to last me 20 years. I have lately taken the view that what I will do is to buy shoes that I think are stylish but - more than anything else - are comfortable. This also means that I won't buy in a particular price range or shoes made by a particular range of makers. As you get older, you get more invisible, so no longer have to buy shoes for other people to look at - if other people ever look at our shoes. It does seem to be that 'comfort' is probably one of the most important features about what we put on our feet. Comfort and style, perhaps. Just some thoughts!
Could you expound on the part of your comment that I have highlighted?
I inferred that to mean you feel shoes at the higher end of the price range ($800+) are more about looks than comfort. If that is your position, then I would tend to disagree.
First, let me clarify the context being leather business/dress shoes; Velcro closure, rubber soled walking shoes, are probably more comfortable than most leather oxfords, but look terrible with a business suit.
In my opinion, I believe that the shape of the last is the major definer of comfort in a shoe (if the shoe is properly fitted). Arch support and quality of insole also play a role. Finding a last shape that fits your foot shape is the most important thing for comfort to me. This is the main reason bespoke shoes fit so well; because the last has be created/modified to match the shape of your foot.
I have also found that lasts made by the higher end shoe makers have more nuances in the shapes of the lasts to better conform to foot shape, regardless of the last style. You can see this simply by comparing a shoe made by a maker like Allen Edmonds versus Edward Green or John Lobb. Whether the difference in cost is worth the difference in comfort is a personal perspective.
I personally don't buy shoes based on what others might think of the shoes specifically. I buy shoes based on a number of factors like: Do they feel comfortable, do they fit my style and therefore my wardrobe, are they well constructed, and are the materials of good quality. Of course the visual appeal has to be there for me to be attracted to them in the first place.
Certainly, comfortable shoes can be found for less than $500, but I can tell you that even though I have Allen Edmond shoes that fit me comfortably, my John Lobb shoes fit like brown on natural rice.
I think it comes down to finding the best fit within your budget.