A: I suspect your shirts may be a little short in the sleeve. Your cuffs should at least half-cover the watch. While shirt collars come in half-inch increments, sleeves come in one-inch increments, so sometimes it’s hard to get them just right. If the next size longer seems too long, you might try custom shirts. They’re not much more expensive than off-the-rack, especially since you’re wearing these brands, anyway. Otherwise, it’s a fairly simple matter to have your shirtsleeves altered by a tailor. Many stores will do it for free. Some dandies actually wear their watch over their cuff, but to get away with this you have to be a mighty sharp dresser, have slim cuffs and wear a dressy watch. A Rolex Submariner is expensive but not dressy. The only cuff it should be worn over is that of a wet suit.