the first watch I BOUGHT was a 1940's bulova art deco design...
I just graduated and didn't have much $. A friend took me to a NAWCC meeting in California and I saw all the beautiful rolex, patek, etc... Of course, I couldn't afford those so it was just a dream.
But then...I saw this unusual watch. It was gold (turned out to be plated), but had a facinating two tone 'checkerboard' face and very stylish lugs. I loved it.. They told me $350 and it was mine! I still have it (needs a new crystal), but doesn't feel right wearing it anymore...just too small after I got used to wearing Rolex, Panerai and other large watches.
Will always have sentimental value for me though.. Twelve years agos when I was divorced, I sold all my watches..except that one (granted it wasn't worth much!). My daily wearer became a Swatch for three years after that!! LOL!!