Are boxer shorts more likely to keep your crack from making an appearance when you sit down?
The reason I ask is…, my son has this problem. He has no waistline, combined with the fact that he forgets to hitch his pants up before he sits down. Since the tightie whities ride kind of low anyway, they come down with the pants.
I reckon boxers have more of a “buffer area”.
Boxers fit loosely, while tightie whities are suppose stretch.
Get him a pair of boxers… just to try out. No harm done.
Sounds like he’s wearing the wrong size, either pants or y-fronts. Too big is as bad as too small.
Just out of curiosity, does your son find it annoying too?
I’ve got a similar problem myself, but I find that wearing a belt works out fine. And either tuck your shirt in, or leave it hanging over your pants.
If you do try to use boxers to compensate, you get into the whole higher boxer problem replacing the buttcrack problem, leading to an esclation in the pants - boxers arms race until the boxers are around his chest. It’ll end in tears ya know 
…and you wouldn’t want to tear your boxers.
…and you wouldn’t want to tear your boxers.
…and you wouldn’t want to tear your boxers.
Good joke dude, but 3 times !
I just thought he was really, really serious about it.
I second the motion to cure the problem and not the symptom. Get him a belt, tell him to tuck his shirts in. Cripes, where’d he grow up, in a barn or something?
<checks OP’s user id>
Wait. Don’t answer that…
A good beer gut outta fix his problems.
Staple gun. Problem solved.
Seriously, though, you might want to suggest he hitch up his pants a bit before sitting down. Hitching them up by pulling on the thigh area of the pants should work well.
Or, use spackle to fill in that unsightly crack. That’s what it’s for.
Belts make the pants heavier so they ride down more. His lack of a beer gut isn’t the problem, he has a macaroni & cheese gut, which is the main cause of the problem.
not to hijack here, but just a re-occuring question that i have. why the opening in the front of boxers and briefs? i thought it was a “shortcut” when i was a girl, but the hubby informs me that i am wrong, wrong, wrong. so what gives?
Supposedly you’re supposed to pee out of it, but I don’t think anyone does.
It’s supposedly the equivalent of the zipper on your pants. Myself, I use neither.
one word…suspenders
Tell him if he can’t keep his pants up, he’ll just have to start wearing suspenders or better yet, overalls. 
Try boxer briefs. The unsung, uncared for but far superior men’s underwear option.
Overalls.
Tattoo underwear on his ass.