I've had a brand new high-end German car for almost a year and some of my closest friends don't even know I own it (I live in a large city where driving isn't that common).

I like to keep a low profile for the most part. I don't want to attract the wrong kind of attention, look like a "young hot-shot kid" at work, etc. There's nothing wrong with women appreciating your success and ambition, but nobody wants to be a meal ticket.

I think women like confidence more than money, but having both never hurts. I once joked to a friend that my luck hadn't improved significantly despite earning much more; he quipped "you were still a guy who was going to make a lot of money back then, you just didn't have it yet."

The most interesting signaling behavior to me is being a hipster. Not having to work is really showing familial wealth and status. Most people don't come from a background where they can spend all day finding cool music and weird clothes rather than working a 9-5.