My oldest watches are this Hamilton pocket watch and Roamer wristwatch.
I don't know how old the pocket watch is......
The Roamer Super Shock manual-wind Gents wristwatch is only 30mm in diameter and belonged to my father-in-law.
It started life as a watch from the 1950s that he wore as a R.A.F. Military Policeman on deployment to Malaya during the Communist Insurgency.
He was a beefy M.P. more than six foot tall and his watch was only 30mm diameter!
It has been through bar brawls, firefights, nocturnal helicopter crash landing in a mangrove swamp, and a fatal automobile collision.
The last event required judicious application of a ball-pein hammer to straighten the winding stem.
I had it refurbished 15 years ago.

Hamilton Pocket Watch and Roamer Gents wristwatch
Regards,
MTF