I did NOT grow up wealthy, at all, but my grandparents on my father's side had money. So I had some fairly rich people, related to me, who I got to spend time with--even though my parents didn't have money, and even though I was the townie in a local day school where I was skiing on ungainly hand-me-down skis and riding my bike to school, as a HS student, while the other kids had brand new skis, BMWs, etc.
But I had rich grandparents who lived on Sutton Place South on the East Side of Manhattan, ate caviar with cocktails, and had a condo in St. Thomas.
One advantage I received is that my grandparents paid my college tuition plus room and board. They wrote a check. My parents contributed nothing. I cleaned bathrooms in order to make spending money. Weird, I know.
A second advantage: my grandmother shopped at Lobel's, a swanky butcher in NYC, and sent home what my mother called "CARE packages" of veal cutlets, shell steaks, etc. We couldn't afford any of that stuff--but we sure enjoyed cooking and eating it.
Third advantage: every now and then we'd visit my rich grandparents in the city and my grandmother would take us to Saks Fifth Avenue to shop. My mother would take us to Robert Hall and Korvettes for a couple of pairs of pants and a few shirts, once a year, but then we'd have a New York trip and end up with someting from Paul Stuart. Heck, in '75 I had a white disco suit from Saks.
Fourth advantage: once every year or two, usually for somebody's birthday, my grandfather would take us all to the Four Seasons. It was a rare but periodic thing; I probably went there four or five times, all told, through my childhood and adolescence. Swanky as hell. We also went to La Cote Basque at least once, and Twenty-One, and La Toque Blanche. This was hugely helpful to me, because it took away the romance--the idea that rich folks were somehow different from you and me. They're not. They just have more money.
My grandmother, a Russian Jew from Brooklyn, was a peasant woman with money. She'd fly Pan Am first class and steal the little salt shakers. She had a whole drawer of those stolen salt shakers in that Sutton Place apartment. That's a peasant mentality. She was loud, wore fur--real fur, mink and jaguar--and had no class, but she was a warm, real person.
So the main advantage I received was attitudinal. I never had any ambition that involved actually being rich, having a lot of money, and hobnobbing with rich people. I had one foot in the door, thanks to those grandparents, so I didn't feel that rich people were any better than me. I was related to rich people: my grandma and grandpa. Their presence didn't affect my daily life very much; my parents had no extra money, so I had relatively little disposable cash. But we had this trickle from the grandparents, and their presence in our lives meant that I felt just fine about being where I was.
When I got to Princeton, of course, I suddenly realized that there was a whole world of rich preppies, true children of privilege, that I'd never encountered and knew nothing about. They had the eating clubs, a whole way of relating to each other and to the Lesser Tribes of plebes like me, and suddenly my eyes opened.