That's the problem: you're optimizing for bang-for-buck. Regular shoes/trainers only go up to a few hundred $, they're cheap enough that, as long as they have a median wage in a developed country, the buyer can optimize for something else like comfort without a significant financial impact.

Bang for buck optimizing is only worth it for certain cost/income combos. In other words: the value of money varies for each individual.

I think I'd argue there is no difference other than possibly as some kind of economic signal which I try and avoid.

I was away for a month and took a new pair of Chelsea boots from a bog standard high street shop with me - didn't want to look to scrufy on a v high profile project.

Walking the 1/2 mile up princess street from hotel to the office in them caused so much pain after 2 days I had to go out and buy some trainers.

Never had that with Loakes - I d agree that paying 2k plus for hand fitted shoes like the city boys wear is probably over kill.