I still have a pair of Sennheiser HD 280 Pro's I bought 20 years ago. That seemed like a lot of money for headphones back then. They have followed me to multiple continents, been on lots of flights and have had their pads replaced and still work great.

I recently moved to Bose NC700s because ya, wireless sure is nice, but I'd be surprised if they last 10 years, much less 20. Still have the HD's though and use them now and then.