Made you look!

Seriously though, I need to buy some new underpants and have never worn anything but women's in my life (except that one time when I forgot to pack them on vacation and had to borrow my brother's briefs, which was a mortifying experience at age 8 ). I gave myself permission to stop buying women's clothing, and now I'm in that terribly embarrassed zone of not knowing how to buy men's clothing. How do you size them? Are they uncomfortably roomy if you don't pack? And how do you stop boxers from riding up all the time?

Thanks!

And how do you stop boxers from riding up all the time?

boxer briefs. Sizing is easy, read the package. Your waist size determines the shorts size.

Boxers normally don't ride up if you wear guys pants. Boxer breifs tend to be better at not riding up and are nice for packing since they have a pouch.

I wear mens everything and BOTH boxer-briefs and boxers ride up on me.

I wear boxer briefs & briefs... both of them feel better and feel more comfortable on me than women's

I've never paid much attention to the sizing, but the waist measurement will be on there, so just match it up to what size jeans you wear. I don't pack, and don't find them too roomy, but then I like some freedom :p I wear boxer-briefs from Topman.

The only underpants I've found that don't ride up are Starter brand boxer briefs... pretty sure Wal-Mart is the only place to get them. I typically buy one size lower than the measurements on the package say, especially if I intend to be packing, because it keeps the packer from trying to crawl down your leg.

If boxers and boxer briefs both ride up, then just...wear briefs.  I do, since I've got the same problem.  I mean, they still make them for a reason, presumably because not everyone likes boxers, despite the increased "cool factor".  If you don't buy the white ones, then you're still ok if someone happens to see your laundry pile, or gets into your pants, they're still not *technically* "tighty-whities".  And they do hold your packer better.

I find the most comfortable are Boxer Briefs. Or Boxer trunks.