The difference is in each man's sartorial knowledge, passion for clothes, and innate sense of style.
Knowledge is more fundamentally important than an enabling factor such as wealth.
Think of it this way:
Two authors each write a book.
One is terrible, whereas the other is superbly written.
The terrible book is published because of factors unrelated to its literary value. Maybe the author was already famous for another reason, or maybe the publishing house determined that this book would appeal to preteen girls and sell millions of copies.
The superb book, however, fails to find a widespread audience and is a commercial failure despite a very positive critical reception. Many people cannot understand it or relate to its subject matter, but those who can are blown away by the writer's ability and become loyal fans.
While the author of the second book does not profit financially from his literary endeavors, he is often approached by people who have read his book and congratulated for having written it. He knows that he is a good writer, since by this point he has been lauded by an understanding few whose intellectual ability approaches or surpasses his own.
The author of the first book may have made millions of dollars and have a movie deal on the way, but whether he is aware of it or not, literary snobs deride his work. They hold it to the same standards as they would the second book, and deem it to be of no value to the intelligent reader.
On Style Forum, we are fans of the second author. We're in the minority, but we have high standards for what we enjoy. Many others will not be able to identify with us, and that's fine. It makes some of us appreciate our strong interest all the more.
Although I haven't been a member for long, I've already seen some posts that showcase personal wealth and some which speak of humbler means. With the conspicuous exception of certain status-obsessed egotists whose posts are best appreciated from beyond the fourth wall, I've found this forum to be quite egalitarian in nature. We all just want to develop our own style so that we can look good regardless of how much money we have.
Conversely, many people with lots of money want to use it to avoid doing things they don't have to do. Choosing and learning about clothes is one of those things. Just as the first author doesn't have to worry about his books being well-received so long as they are successful, some wealthy individuals may prefer to go to one fairly reliable shop and buy three of everything the sales associate recommends to them. They'll have the clothes and the means to buy more, but without knowledge or passion they will not be truly well-dressed.
In a nutshell, it's because we know more and care about learning all that we can. Money is irrelevant as long as there is enough to support a reasonable outlet through which to express that knowledge and enthusiasm.
Oh, yeah, and also "sprezz," I guess.
-VF