When compelled to whittle down to three, I regress to pieces from early in my obsession - it's a threesome that hasn't changed despite many watches acquired since that I like very much. Each of these was a formative addition to the collection, I remember the hunt/the find for each of these in detail and I still remember the thrill of putting them on my wrist with unusual clarity and vividness.
1. Zenith A 3818 - this was the watch that started me down the vintage path, chance find by a vintage watch ignoramus at an estate sale. Still the best example of this case that I have ever held.
2. Zenith A 386 - pictured here was my first of this reference. I have found better examples since but this was a coup de foudre.
3. Zenith Cairelli - big, clear and exotic, I have never found a tool watch with more panache.