I can speak from personal experience on two industries - financial markets and aerospace. In aerospace you can wear whatever, at whatever level you are, and no one cares. Your watch is totally irrelevant.
In the financial markets, it depends one where you are in the structure. If you're front desk (or you want to be) and working your way up, with dinner and golf with clients and such, yes, you pretty much need the nicest watch your bonus or your credit card can get you. If you're middle or back and aren't working to make the front desk, no one cares what you wear. It won't determine your advancement. If you're top of the pile, you can pull off anything you want, but you're also not going to be asking what you should wear in a forum like this, LOL.
In NYC and LA, yes, pretty much everyone will judge you based on what you wear, and not just on your wrist. In NYC we called it the "once over" and girls get it more than guys. If you're "last year" or "no year" or whatever some girls won't deign to meet your eyes let alone talk to you. It's a very friendly, welcoming environment. 🙄
Now that I live in Seattle, no one cares what I wear anymore (on my wrist or otherwise). My pink hair is much more likely to hinder my career advancement than my clothes or my watch.
