I have vacubags full of clothes I can still wear since my 30's (there were years I could not fit in them but when divorced most of them fit. When I do drag something vintage out some woman always tells me that I made a great find...
A classic collection of Charlie Harper shirts and Capri pants
Most of what I would still wear are 2000 up/. golf shirts, dress shirts. I have about 20 Italian designer shirts, never worn, but If I drop 10 more lbs.....