Not that often. Not only were full crowns rather heavy, they were often the most valuable thing the monarch owned, partly for the symbolic value the particular crown had but mostly because of all of the jewels and precious metals. Thus, wearing it from day to day would have been a huge risk. (Also, depending on the state of the royal finances, you might have had to pawn them…) So most of the time, the crown stayed in the vaults with the rest of the royal jewels and plate.
A further complication is that monarchs seldom had just the one crown. To use the English monarch as one example: St Edward’s Crown was the oldest of the Crown Jewels and goes back all the way to Edward the Confessor (hence the name), although parts of it supposedly go back to Alfred the Great. This crown represented stability and legitimacy of succession, as it had been used for every king pretty much between William the Conqueror and Charles I, so using it was very important: hence why Henry VIII used it to crown Anne Boleyn, a very public statement about the way things went. Incidentally, Parliament sold the crown in 1642 during the Civil War, and no one knows where the original went. (Charles II had a replacement made, and then Colonel Thomas Blood stole that one, and so on…)

Needless to say, you wouldn’t dream of using this crown except for coronations, so kings acquired other crowns to be used on different occasions. (Edward III, for example, had no less than nine crowns and a dozen circlets, because if you’re going to try to conquer France, you need to do that in style.) So when would a king wear a crown? Well, any major public event – a religious holiday, the installment of a bishop or the dedication of a church, a session of Parliament, meeting another monarch, making a pilgrimage, etc. etc.
For ordinary fancy occasions – your state dinners, your feasts, your dances, your earlier monarchs went with circlets or coronets. But fashions change, and once we get into the later Middle Ages, you start to see more of a preference for fancy hats as day-to-day wear. My personal favorite is Henry IV’s rather snazzy red number:

Now that is a hat that screams “I may be a usurper whose actions will lead to the Wars of the Roses, but you have to admit, I look damn good.”