When buying clothes, you need to measure the three dimensions, but I've never heard of anyone buying underwear who needs to measure their, well, "dick size".
If clothes are a bit bigger or smaller, it's just a matter of showing a little more or less skin. But if the underwear doesn't fit, being a little small is not that big of a deal since they have enough elasticity (I still vividly remember the scene from "Days of Being Wild" where they blow up a balloon). However, if it's too big, then we're talking about whether it will fall down, leak, or even win a prize!