My experiences have been very mixed mixed.

One family friend of ours is a well-known actor. He’s got a few houses, nice car, housekeeper, etc but he always dresses like he’s about to walk into a dive bar; old jeans, t-shirt, lace up leather boots. Doesn’t act like he has money at all. We also have a few other family friends like this that aren’t famous, but same concept; they don’t look or act rich, but they’ve got money in the bank.

I’ve also met quite a few others that make sure they flaunt it any chance they get. Some even go as far as hash tagging #RichKidsOfInstagram on every post they have. They look like major tool bags though.