Like most boys, I first wore tiny, colorful briefs. I have no idea why we invariably start our children in tight drawers, especially since up to a certain age male underwear isn't especially necessary, except to prevent skid marks on pants. We're just trying to establish an understanding that one day you will need to wear something here, so you might as well get used to the idea, kid.
Then comes college. That's when I became concerned with how underwear looks more than anything else, because I had hopes that women other than my mom might see it. I started wearing boxers because they were "cooler" than briefs, which is asinine when you think about it. I am rarely seen in public in my underwear. I invariably present myself either fully clothed or buck naked, but I suppose in those few transitional seconds, boxers are more aesthetically pleasing than briefs. Young men don't really need underwear structurally, but they do often require physical props to help them tell the world who they are and wish to be. Boxers are the perfect underwear for men who still worry about what other people think of them.
Middle age and gravity take care of such petty concerns. I've written in these pages before about my most singular familial trait: a scrotum that looks like lemons dropped into an old plastic shopping bag. I knew my years in boxers were numbered after a couple of memorable camel-toe incidents—there's nothing like seeing the horrified look on someone's face and then following their stare down to your crotch—and that final day of reckoning, when my balls fell out of my pants on busy Elgin Street in downtown Ottawa. It wasn't the wide eyes that tipped me off; it was the breeze. Those were the winds of change.
I had been skeptical about boxer briefs, which seemed to me like the suburbs of underwear, offering every possible inconvenience. I couldn't have been more wrong. Boxer briefs do everything underwear should do; they are the height of our undergarment civilization. They're immensely practical, offering support as well as protection from old-man concerns, like thigh chafe, and keeping the front of your suit from looking like a billiards-table pocket. And they offer the relative attractiveness of boxers without the bunching up or any of their goofy smiley-face "personality." A pair of black boxer briefs makes the middle foot of my body look like the knot in a bow tie: It's the illusion of precision and control, the anchor that, however tenuously, keeps everything else about me from falling apart. —Chris Jones Esquire Magazine