It's not a matter of pretentiousness. It's just a matter of what they buy. If it was pretentiousness they'd wear tuxedos everywhere and you could spot them easily. But shoes and watches (and glasses, but you can't count on people wearing glasses at all) are things people tend to buy the best that they can afford.
Good looking watches and shoes go with everything, if you're dressed up they make you look better, if you're dressed down (which being as this was in Tucson most of the time when I delt with investors they were dressed down, nobody here wears a tie if they don't have to) the don't look wierd. And well crafted watches and shoes are more comfortable to wear and last longer. Thus if a person is in the investor class, if you look at their wrist and their feet when you shake their hand you're probably gonna see at least $1500 worth of hardware, not pretentiousness just functionality and comfort.
I have these friends in California who are worth millions and you sure couldn't tell by looking at them that they are rich - I've seen her shop at Target and he wears regular shirts and a baseball cap! Of course, he made his millions by being a self-made business owner and this is just pure crap by one worthless politician who doesn't even make his own $200k without MARRYING for it!