Wow, some seriously AWESOME watches in this thread. And good variety, too. Nice to see some outside the usual suspects like the BR, Mido, and Bulova.
I'll bite and make a contribution, since I just recently upped my watch game!
Tudor Black Bay GMT
I've had it for about 2 weeks now. My first luxury watch and I'm blown away. My true love has always been the Pepsi GMT Master II (not the new ones!), the ref 1675. Realizing I could never see myself spending that much, probably ever, I turned to the Tudor Black Bay line, and in my mind was settled on a Black Bay Black as the "grail". Thought it was going to be "the one" for several years.
But then when the Black Bay GMT was announced this year, I knew instantly it was the watch to end all watches for me. I had some funds from a small sailboat I'd sold recently and in the back of my mind had been sitting on them for a watch purchase, someday. Essentially not ready to pull the trigger but already allocating the cash.
I decided to just do it. It's a LOT of money to me, and something I thought I'd never end up actually doing, but it's something I'll get great enjoyment out of everyday. I figured life is short, nothing is guaranteed, and might as well start enjoying this life-long piece now.
I'm 30, close to 31, and expecting a first child (daughter) any day now. Like
vbrad26 I seriously struggled with whether I should go forward with it or not, especially considering the kid on the way. My wife kind of gave me the extra push I needed. She said "you've been talking about this forever, you should just do it and get it over with". And so I did and at first I was like WTF have I done, but after a week or two on the wrist I couldn't be happier. And it will always be sentimental to me having bought it in the birth year of my first kid (I've long thought attaching watches to significant events is a great idea).
I've had a few other mechanicals previous to this with ETA and Sellita movements in the $500 price range, and everything about this watch blows them out of the water. The design, details, fit and finish, and movement are phenomenal. The movement is buttery smooth, nice and crisp, and the features are basically identical to the Rolex GMT's. My wife and I also love to travel, so it's also symbolic of that, and I hope to bring it on many trips to come.
Sorry, didn't mean to write a book, I'm just... excited!
P.S. There were a handful watches before the Black Bay obsession, some of them that looking back make me cringe a little. Been wearing a watch of some sort every single day for the last 12 years. Happy to share a few others when I have a chance