Depends on the width of the shoe and of your foot - for most Italian shoes, Rider's list is the one to go by. I wish more makers would acknowledge that - a 45 is NOT a 12 in most makes, drives me nuts... The marked sizes on most brands work only for people with ideally shaped, and probably narrow(ish) feet. For more standard widths/last shapes, shift the list up 1/2 size.
Quality counts, whatever our age, profession or bank balance.
Men who know there stuff would look at them and not take you seriously. On the other hand a pair of Crockett & Jones Hangrades (E.G. Weymouth in antique brown and then Aintree in Black alternated) will be a stand out choice noticed by the discerning and quietly admired by those with no idea.
l love those style of shoes. l have afew Pradas that look like those. The problem is that they are only average quality (not bad though). l say; wear them with your suits to the bank. There is nothing wrong with those.
to be honest, I've quite new to shoes but i find them very plain and boring. If you're buying Prada or Gucci, its 95% goes to buying the label and 5% goes to quality and craftsmanship