Horological Meandering

mkvc
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On a strap with a regular buckle, you don't have to make a decision.

Just buckle it where it feels comfortable and if later in the day it's too loose or tight, change it. (I am fussy about fit and often have to cut additional holes in my straps.)

Different straps will require different levels of tightness. Generally, I have found that a medium-stiff strap can be worn loose because it will still hold the watch in place. A flexible strap may have to be tighter to prevent flopping. A very stiff strap may have to be tighter (or at least feel tighter) to get it to curve around your wrist. Obviously, the weight of a watch head is also a factor.

The real problem comes when you have a bracelet (without micro-adjustment) or a deployant clasp. Then whatever decision you make about tightness is, so to speak, binding. You have to make sure there is enough room inside the bracelet for it to be comfortable when your wrist is at is largest (for example, on a hot afternoon after standing up all day). If that makes it too loose at other times, you either have to decide to live with it or reject the watch. I have found that a reasonably light watch with a reasonably flexible bracelet and a good adjustment mechanism can normally be sized so it works for me. However, if the watch is too heavy, the bracelet is too stiff or the link configuration doesn't allow for an accurate original fit, I have to give up.