text: what is the difference between underwear(briefs) and boxers and when to use what?   boxers are like short, just a lot lighter.  briefs snuggles your groin and keeps everything in place.  there is no real determination to what to wear but it's just a preference.  however, i have known doctors to ask couples for the guy to wear boxers if they are planning to have a baby. it's a lot easier for the penis to breath.  but it's not required, just a suggestion.