I’ve worn a lot of watches in a variety of bands. Metal, plastic, nylon, and leather bands have never felt comfortable.
On a whim a few years ago I tried a Timex Expedition which features a velcro “fast wrap” band. The difference is amazing; my arm is able to rest on surfaces without something digging into it, and it’s significantly easier to take on or off than buckled or metal bands. The only major downside to the velcro is the breakdown of the soft, micro-loop sides which happens after a decent period of time.
The watches are never more than about $30. They’re varyingly small, comfortable and come in a lot of varieties, including analog versions. Putting on any other watch just feels out of place now.

