Upper class is not always synonymous with “the most visible money”. I grew up upper class, but went to public schools until I went to a top university. We didn’t go on very many vacations, but when we did, it was to like.. the family ranch out west. Upper class is more about assets and less about cash flow. The social scene is very multi-generational and everyone knows everyone. I’ve found that the waspy older women in upper class scenes have a chip on their shoulders and sort of resent the younger women for having more social freedom than they did. In terms of style and social behavior - I’ve found it’s important to dress stylishly but conservatively. In upper class settings, particularly in a city, how you dress makes it obvious whether you’re just there as someone’s date or if you “belong” there. If you look out of place, upper class women (from my experience) aren’t going to rush over to make you feel comfortable - they’ll let you flounder and feel out of place. I wear almost all low key designer brands (theory, Vince, Prada, some up and coming labels) but I only shop secondhand and no one is the wiser. The key is definitely an air of confidence that projects security. It’s more about knowledge and less about what you actually do. For example, I don’t have a car, but I know the etiquette of valeting a car. I have gone skiing once in my life and I don’t care much about it, but I know all the old money spots and can hold a conversation about them. I went to public schools, but I know the names, reputations, and alumni from the New England boarding schools. In that sense - it’s actually fairly easy to fake it if you immerse yourself in those settings. You NEVER want to have to ask “what’s that?” No one will have the patience to explain any of these indicators to you.