In my experience at most 25% of the captains go topless. Maybe "most go topless" in your experience because you suggest it?

I hate being without a headset in cruise. It's just too loud, and I miss calls all the time.

The headsets aren't as comfortable as my telex 850, but I like not having to keep up with a headset anymore.

Worst case, fly a trip or two with the provided headsets, and buy a nice one if you don't like them. There are standard plugs in the plane, so you don't have to buy a 5 pin connector.