Modern pilot’s watches don’t really have a practical function today. In the years from the 1920s up until the 1950s, they were essential parts of equipment, and so gained their characteristics of large size, and long leather straps so that they could be worn over a flying suit. Today even sports pilots have all sorts of high-tech instruments that make a mechanical watch an obsolete accessory.
But there could be a niche market for traditional pilots’s watches, amongst those pilots who fly the very simplest aircraft: paragliders and hang gliders. As, I presume, the people practising these sports are crazy about flying, it could be that they could be interested in a large, old-style pilot’s watch with a long strap so that you strap it external to your flying jacket and see it easily while you are in the air. They are often interested in beating their personal best for flight duration (as long as possible) and so a marker on a rotating bezel would help them see at a glance how long they have been in the air. If it had an extra complication, it would have to be a mechanical altimeter, or a chronograph. The same sort of characteristics would be good for other sports as well, those in which you are doing something with both hands, such as cycling. And I would definitely prefer a display caseback just for the added visual interest and beauty that it provides.
In the photo, one of the few watches that comes close: the 55mm Laco Aviator Observation Watch.