For a while, I had two matching
Black/Gold and
Silver/Blue Fossil Twist watches. I had gotten a $100 VISA gift card from a credit card deal, but through a mix-up, got an extra gift card, and was debating between the two color schemes. So I got both! (They were around $100.) But... fast forward at least a decade, and I never wore either any more, and they have been sold.
For my 35th birthday, I bought myself a
Citizen Eco Drive Perpetual for about $245, and that was the watch I wore the most over the next five years, and I still love it and have it on standby.
But for my 40th birthday, my wife bought me a Fossil Explorist Q HR (4th generation) smart watch, and that's the watch I've worn
just shy of every day since then! Of course, it's not as super old-school cool as a proper mechanical watch, but I've found several digital faces that I really like, and occasionally I even use the other features ;) It is useful for information when I ride bike, tracking heart rate, speed, elevation and distance!