In the early days, a pilot's watch was mechanical, had a large dial and a big crown so you could adjust it with gloves on. In the late 1950s, Rolex came out with a GMT model specifically marketed as being for PAN AM pilots. Citizen have had models with a built in whizz wheel on the bezel and Brietling had one with an emergency locator transmitter.
Most of the special functions these days can be performed on a smart phone or are built into the aircraft. Most things I do on a basic pocket calculator or use an app on the electronic flight bag. As far as watches go, I use a Garmin Instinct 2X which is probably a bit of overkill but what I like is the large display. Having the day of the week on the home screen is useful because working irregular patterns it's something I need to look up, I've got a UTC display which is useful for knowing the validity of weather forecasts, I can easily synch with the local time on arrival and being solar powered it takes weeks to rundown before it needs plugging in. The other built in functions, I seldom use. Being made of a composite material it doesn't set off the metal detectors either.