I knew there had to be a thread like this on here!
I was flipping through this thread and skipping 20-50 pages at a time and ran into one of my same watches twice! It was a Zeppelin and my first automatic movement. I wanted something with a power reserve and have been really happy with it.
I think my next purchase years ago was this Bulova. I have a rose gold wedding ring and wanted a watch to match. I've also always loved watches that dress up more than the average dive/pilot watch. It's a quartz movement, but I still love the look.
And my most expensive piece is a Day Date I inherited from my grandfather. I received it a little banged up (missing lume, damaged crystal) and had it sent off to Rolex for servicing. They dated it at about 1979.
They said I could change the color of the dials if I wanted. I wasn't a huge fan of the 'old man' gold on gold on champagne so I went with a blue face and it really struck me. I would've never bought this for myself, but having sentimental value and being able to create a unique piece really made me happy.
I also have a leather strap I can throw on it to make it even more subtle.
And for a little watch porn, my grail...