Wealthy, unattractive men often have no problems approaching beautiful women. Aside from the obvious buying power money has, very often the kind of man who amasses great wealth has some kind of never give up, inner drive, determination, stubbornness, etc... which translates into other areas. Like getting what you want as far as people go.
If you look at the broke, works as a Walmart greeter guy, chances are his vibes will reflect his situation... not very confident, probably pedantic and set in his ways, fatalistic, etc... people aren't usually attracted to that. Old, broke poets and painters sometimes do okay with young women for awhile because of the whole "romantic" image they have.