I'm kinda getting out of vintage watches as, believe it or not, I’ve actually lost interest in them. I've sold off a fair number of them over the last couple of years, but will be keeping a ‘core’ group of them for daily wear.
These first two I like, but will likely part with. First one is a Hamilton 88-W-800, US Navy, 1940's. 987S 17 jewel movement. Not sure if those Mercedes hands are original to the watch, but it's the way I bought it 20 years ago and I happen to think they look pretty good.

Hamilton 88W-3 by
Vince Lupo, on Flickr
This one is from 1917 - unmarked 15 jewel Swiss pin-set movement in a sterling silver George Dimier case, David Boettcher watch strap. Keeping pretty good time for 103 years-old.

Suisse2 by
Vince Lupo, on Flickr
One that I just sold -- 1927 Waltham Chevrolet dealer watch.

Waltham1 by
Vince Lupo, on Flickr
Sold this one last month -- 1916 Elgin trench watch, David Boettcher strap.

Elgin Trench2 by
Vince Lupo, on Flickr

Elgin Trench3 by
Vince Lupo, on Flickr
One of the prettiest watches I've ever owned -- the watch is from about 1917, the holder is likely from about the same time. I had a jeweler add the 14k lugs so it could take a standard 16mm watch strap.

Elgin Pendant1 by
Vince Lupo, on Flickr
1951 Seamaster bumper automatic - nice watch, sold it a few years ago.

Omega Seamaster8 by
Vince Lupo, on Flickr
1970's Cartier, from the Must collection. Neat watch, had a wood face and sides, sold it a few years ago.

Cartier2 by
Vince Lupo, on Flickr
1940’s Cortebert in an 18k case, a real beauty. Kept great time.

Cortebert1 by
Vince Lupo, on Flickr
Late 1950's-early 1960's Hamilton (Swiss movement), 14k case.

Hamilton14K-7 by
Vince Lupo, on Flickr
One of the few 'good' watches I've ever owned - Patek Gold Ellipse, mid-size, in 18k white gold case and buckle. Beautiful in its understated-ness. Sold a few years ago.

Watches30 by
Vince Lupo, on Flickr
1930's Huber Nautica -- this one's a keeper. Paid $100 for it.

Huber Nautica by
Vince Lupo, on Flickr
Most of the watches I have are vintage, and as a result are on the small side (compared to today’s watches anyways) and not particularly expensive. So I never have to worry about playing the ‘one-upmanship’ game, as I don’t even think I’m in the game to begin with.