For manual winding watches, it is recommended to wind the watch every morning or every night.
Most manual winding watches have around 40 hours of power reserve, so waiting two days to wind it will make it stop. For automatic watches, you don’t have to wind it at all if you wear it every day.
With manual winding watches, most watch manufacturers suggest turning the crown between 30-40 times to get the watch fully wound again if it has lost all power. Manual-winding calibers usually have around 48 hours of power reserve. However, it is not recommended to wait for the watch to stop before rewinding it.
Pick a time of day and stick to it. Morning is common because you start the day with a full reserve. Most manual calibers hold something like 36 to 48 hours, so skipping a day is usually fine; skipping three is how you find it stopped in a coat. Automatic wristwatches wind from wear. If you only put one on at weekends, a few crown winds on Friday night will keep it from sitting drained.
A pocket watch in daily use should be wound fully, then carried. Do not top it up every hour. Do not yank the crown sideways. If it used to run a full day and now dies by late afternoon, that is a service symptom, not a winding schedule problem. Same if the crown feels gritty or suddenly very easy. Those are bench questions, and an estimate for them is free.
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pocket watch guides (Collector’s Corner).