If you can vote, you should not be wearing boxer shorts. If you are legally allowed to drink, you should not be wearing boxer shorts. And if you're required to wear pants on a daily basis, you most definitely should not be wearing boxer shorts.
Of course we want you to wear underwear (the morals and logistics of going commando is another topic for another day), but boxers are the most impractical, childish, least sophisticated, and worst-fitting option in a marketplace rich with possibilities. What's more comfortable and stylish than boxers? Literally thousands of options. Which is why we're left to wonder why there are still men out there (you?) who choose to wear bunchy wide-leg cotton shorts or worse, said shorts adorned in Christmas plaids, cartoon characters, and jokes that were played out by the time you were 13. (There's bananas next to your dick! Get it?)
Boxers were more acceptable—and maybe wearable—in the age of JNCOs and the standard suit fit was two-sizes-too-big—but we're living in leaner times. Straight-fit trousers in 2016 are much trimmer than their '90s counterparts ever were, bringing pant fabrics closer to us—and our thighs—than ever before. But with their loose fit and ballooning fabric scrunched into one elastic waistband, boxers bunch underneath everything, from slim-fit trousers, jeans, and even shorts. This is bad for two reasons: 1) It's uncomfortable as hell and 2) forces any excess fabric to muffin top over the sides of one's pants. The next time you go to reach for a cup on a high shelf or bend down to grab your weekender bag, do you really want the world to think you're smuggling a chef's toque around town?
And there's no menswear piece boxers ruin more than a suit. Wearing tailoring successfully comes from cutting a razor sharp line; boxers create a bulky mess around your upper thighs that wrinkles your pants and tells the world—no matter how much you iron—that your shit just ain't all the way together (or you have an actual load of shit sitting in your trousers). Should you be the unfortunate man who rips his pants at a wedding while busting a move to "Hey Ya!", there's only one type of underwear with enough space between itself and your legs to make a catastrophic dick slip even a remote possibility. We know it's unlikely, but are you really trying to risk it?
Maybe the only thing you care about when it comes to underwear is what your romantic partners think. We say it's always best to look out for number one (that's you) first, but when it comes to pleasing, well, anyone. Using that thinking, boxers still find themselves at the bottom of the basket—especially in a first encounter scenario. You say they're masculine, unpretentious; we say they're the uniform of your overzealous teenage boy self. Point is, there's nothing to gain from wearing boxers in a romantic setting. What does the reveal of some wrinkled junk-blouse as soon as you drop your pants say? The revelation that you really, really like puppies/shamrocks/oars?
There is one situation in which boxers are better than any other underwear, even more socially acceptable: the pants-less hours when you wake up, make coffee, eat breakfast, read the paper—really any time you're not actually in public being seen by other people. (We'll also say that if you're fleeing a burning home, you're good with just boxers.) But for the rest of your life, boxer-briefs are the best of everything. And thanks to places like Uniqlo, they're even the least expensive option in the book. Sorry boxers, but in the bout between you and every other kind of underwear, the result is almost always a clear-cut knockout.
Your boxers solution comes in the form of a pair of black boxer-briefs. You'll be hard pressed to find a person who would take serious issue with stretchy cotton, slim-cut (just enough to hug the thigh) style that perfectly toes the line between conservative and sexy. Briefs (street name: tighty-whities) can be a viable option so long as you actually avoid buying them in white or in retina-searing shades of neon or over-the-top patterns. (They also eliminate any risk of creating the dreaded horizontal crease underneath your suit where your boxer-briefs end, an issue that can also be resolved by buying boxer-briefs in thinner cottons or poly blends that sit flush against your leg.)
Be part of the solution. Stop wearing boxer shorts.