This is always something that has confused me, and I’ve never been sure what’s the best way to go about doing this. When wearing a watch with a cuffed shirt, should the shirt cover the watch? The reason I ask is this; when I wear it under the cuff, it means having to unbutton the cuff to get out the watch (which feels counter-intuitive), when I leave the cuff open on the largest width, it doesn’t match the other hand or is too wide, and when I wear it on the outside it just feels wrong – as if I’m trying too hard.