Yeah, I've been into watches for probably as long as I've been into cars, which must be about 25 years or more.When I was very young I was obsessed with the transformer-type watches. As I got a little older (~10-13), I had a huge fondness for the first generation Timex Ironman and Swatches. Both were quite cheap, but on my allowance of like a dollar/wk, it took some time to save up for them. As I got older, I also acquired any number of cheapo timex, casio, and fossil watches. They served me well, but I always wanted something a bit nicer. Something that didn't look like trash a year after I got it.
In the last 5 years, I've finally been able to get some nicer watches, though I still use a throw-away for the gym. My parents got me a nice Omega Seamaster dive watch and about 2 years later, I bought myself a brown Hamilton Jazzmaster Maestro. They have been great watches, especially the Omega. I was recently in Iceland and came across watches made by
JS Watch Co in Reykjavik. I was very close to picking up one of their hand assembled watches, but didn't feel comfortable at the time dropping a couple grand.
Eventually, I'd really like to a Gulf edition Tag Heuer Monaco, but those are quite pricey. Maybe when I reach the next level of promotion at my company I may consider it. I think the next watch purchases I will make will be on the cheaper side--a luminox and/or Casio G-shock (I have always wanted one since I was a kid, but sort of settled on the Ironman instead). Tissot, Oris, Breil, and Victorinox also have some nice watches I have eyed up over the years as well.
I may need to get a watch case like the one pictured above at some time in the future.