Great thread. In addition to some excellent suggestions above, here are some things I have which are decades old ...
My late Dad's Pulsar watch. Not as flash as a high end name brand. Wafer thin, simple face, must be at least 35 years old.
His Crombie overcoat. Doesn't see much use in Texas but will always keep it.
His RAF issue aviators from the 1950s
My late Mam's Parker 51. Over 50 years old and works perfectly.
Frye harness boots over 10 years old
Levi denim jacket. Bought in 1988
Avirex A-2 and Schott perfecto bought in 1989
Wayfarers bought in 1989
Harley Davidson from 2000
Fujica film camera from the 1960s