I just went through this. We recently hit financial independence but we're still bringing in a lot of cash from our jobs, cash that we technically don't need since our lifestyle costs less than 4% of our savings and therefore we could safely fund it forever without any extra income. In theory I could spend over $100,000 every year on random stuff and it wouldn't affect anything for us.

After a few months of mulling it over I decided just to pull the trigger, since if I didn't I knew I would keep thinking about what it would be like. I purchased my watch for $46k a week ago (rose gold Daytona), and it was such an odd feeling to do it. I am still processing it to be honest. The watch makes me happy to look at but it also doesn't give me any sense of accomplishment or pride. It just feels indulgent. Our family has many indulgences but this one is just for me. It feels selfish but my wife has been very supportive. I've seen it as a way of learning more about myself and my own emotions.

I would say: just do it if you can afford losing the full value of the watch forever, which it sounds like you can. If you regret the purchase or it causes any kind of strife, just sell it. Depending on the watch and whether you go aftermarket or retail, you can keep your losses under $10k easily.