How do you know when jeans are the right waist size? Sounds like a stupid question, I know, but let me explain. I've always worn my pants on the low side, partly due to fashion and partly because I was overweight. Now, not only do I feel too old to wear my pants that way, but I've also recently lost about 40 pounds. I'm not used to wearing normal sizes, and most pants I try on feel too tight even though people around me say they are still too big. I've heard some people say that if you can fit two fingers in the waist then it's the right size, but this can be interpreted in a couple of ways, so I don't know.