Girls have it so easy. Their underwear's best use is when it's worn as outer-wear, with nothing else on underneath it... obviously. For a guy though, underwear's best use is functional, to be doing what it needs to do under the covering we call "clothes." This is why we wear the same pair for days (erm, weeks) on end, and why (when we're alone), we wear nothing else. We know a lot can be deduced from what underwear we choose to wear though, and we won't compromise once we've made a choice. Underwear loyalty is everything, which is why the question about what we go for in underwear is actually quite a test of intelligence, maturity, character, and (sometimes) what 80s Saturday morning cartoon still inspires us. Forget 20-question quizzes in "Does he really love you?" magazines. If you want to figure a guy out, just ask him: "boxers or briefs?" You'll know all you need to know.
Now I've spent a long time thinking about this, and this was the best I could come up with to explain my rationale for continuing to answer the question "BRIEFS." We may not win the battle, but we win the war. Sure, boxers give you room, they're loose, comfy, and let you move and "readjust," and they are great to wear on their own as if they were shorts, because they come with a front flap (which just makes life easier). But they have a lot of flaws. One, they bag up under your pants and you got to keep adjusting them. Two, clothing makers decided that since men were wearing them like shorts anyways, they might as well start putting buttons to fasten them, which just makes "life" more of a chore than it should be. We could live without those pesky button flies all together, we don't need another set on our underwear!
The truth is, we like briefs because they're more supportive and easier to wear, but we will wear boxers just because they look cooler and are comfier. This is why "boxer-briefs" were invented, and are the obvious compromise. They may just be the ultimate winner here, and the most ingenious idea ever, but we're not discussing the subtleties of the so-called "boxer-brief" because it's not a part of the dualistic question posed.
But enough about function. Let's talk about style. Obviously, boxers come in a wide variety of colors and pictures, and briefs have tried to make it with the colors but it just comes off as if you've color-coded your week. The funny thing though is, there's just something more "mature" about boxers, so many guys wear them just because of that, even if they have cutesy little pictures on them! It's like the life cycle of the average male's underwear goes full circle. We start out as kids wearing Ninja Turtles briefs and then grow into "tighty-whities," and then maybe we either go into the land of colored briefs or we go full-tilt into Boxers. We're constantly on the run from the tighty-whitey, and why not? It's tough to shake that "just escaped from the ward" look every time you catch yourself in a mirror when you're changing. But we still like having pictures on our underwear regardless of age, especially at the boxers stage.
Once you've made the decision to continue with briefs to their next technicolor evolution (one color for every day of the week) and take a step into that proverbial locker room, you're still not sure you're going to be dwarfed by the guys already jumping on the boxers bandwagon. But when they reveal theirs and they're full of all these cutesy "flying toaster" or "valentine heart" cartoons, you'll be glad you're a briefs-wearer. Of course anything flannel or plaid and you're screwed, but then again, at least you can easily get at the merchandise without resorting to pulling down your underwear like you did when you were five.
But which is better? Who knows. What do I wear? I wear briefs. My eight-year-old self wore briefs. I was raised on tighty-whities, mostly around my waist, sometimes under my clothes, and a least a fraction of time on my head. Briefs have always been there for me, they gave me support and comfort through the hard times, they picked me up when I was...well, getting a wedgie, and whenever I adjusted my underwear in public... it was always a "snap."
That's why I was, I am, a briefs guy.