Headphones are always going to be an analog process. They’re the end of the audio chain. It’s true that they had excellent headphones in the 1980s, 1970s as well. That’s why a few of us keep recommending the AKG 240m’s, they’re basically unchanged since the late 1980s.
The thing about analog is that the quality of the device makes a huge difference in the sound it reproduces. A CD on a midrange player through good headphones sounds “better” and more transparent than 80 percent of turntables that were in use. When you spent a bit more on high end cartridges, quality amps, and great speakers, a recording on vinyl could beat a CD. Most people didn’t do that.
When it comes to headphones, spending your money on a quality driver, and saving money by not buying wireless, makes a huge difference. That’s why my old AKGs can sound better than 500 dollar wireless cans. Find a good set of flat frequency response wired headphones, that’s the best way to hear the benefits of lossless. You might actually be able to tell the difference between aac and 24/96 uncompressed. I can, and I’m old and my hearing sucks.