Oh, that's a fun idea! Do accessories count?
I get to choose a vintage wrist watch for myself as a Christmas gift from my mother this year, so yesterday I went to a small store that specializes in old watches, run by a charming, excentric old German gentleman, very sharp, talkative and opinionated, who cast a brief look at me, asked what I was looking for (small, men's wrist watch for everyday wear, steel), immediately pinpointed what he thought would suit me, judging by my clothes and general style, and was completely right.
So he produced a few 1940's watches, one 30's and one 50's, all with steel cases, Arabic numerals, round, light and relatively uncluttered faces, which was pretty much exactly what I had in mind. We spent almost three-quarters of an hour looking at watches and chatting merrily about different styles, eras, brands and types. On Friday or next week I'm going back to pick up a mid-40's steel case Zenith, cream-coloured dial with a small, subsidiary seconds dial, and have a steel chain bracelet fitted.
Pictures forthcoming, I hope!