That was it. After 20 years and dozens of pairs of boxers, I decided in that moment that I was done. It was time to dump the lot and finally switch to boxer briefs.
Yes, this is actually the story about how I left boxers for boxer briefs.
Since probably the Second Grade, I have been wearing boxers. My father has always worn them, so have my grandfathers. Frankly, I didn’t know any guy who didn’t wear boxers until I got to college. I had the cheap ones from Target, the “designer you’ve never heard of” ones from T.J. Maxx, and (best yet) the ones from Brooks Brothers that were made of the same material as the dress shirts I wore to school every day.
And so for a not so brief phase in Upper School, I had twelve pairs of Brooks boxers that matched all twelve of my Brooks dress shirts (yes, I know how nutty that sounds and no, I’m not proud of this). I felt like an adult not having that annoying Dillard’s brand plaid or the always mature SpongeBob boxers. This worked out nicely for several years…until I started buying slimmer-fitting pants.
I got my first “skinny” jeans back in 2011. They were these really dark J. Brand jeans that I bought at Barney’s 25 minutes after securing my summer internship at Departures. It must have been 90° outside because I was sweating so badly under my blazer that I refused to take it off while the salesman fitted me. I just remember calling my friend and telling her I bought these jeans that were super skinny and her telling me that they would show off my butt really well.
But I just didn’t feel right wearing them. They were too “hip” for me and so after only a dozen or so uses, they went right back into my closet.
In the meantime, I fell hard for the Brooks Red Fleece chinos for Fridays at work and the weekend. I loved the feel, the colors, everything. Plus, it turned out that I actually looked good in a more fitted pant. The only problem? The boxers kept rising up every time I put them on.
So I responded by developing a routine: boxers, pants, hand holding up pants while I used other hand to shove boxers back down and deal with any rip that might occur in the process.
Then about five weeks ago, my friend Dean (yes, as in the one who asked me to write for this blog) was going through my closet (because don’t all friends who have only known each other a few weeks do that?) and dammit if he didn’t find those jeans! Immediately, he “politely” suggested I reconsider wearing them again. So while he waited in my kitchen, I jumped up and down in my bedroom as I attempted to get them on. And then there was the noise of ripping… accompanied by a burst of laughter. Upon telling Dean I still wore boxers, he less politely insisted I make that switch sooner rather than later.
So I started “researching” the boxer brief the next day. Esquire and GQ raved about them in articles going back at least a decade. David Beckham liked them so much that he had no problem showing them off on a five-story billboard in Times Square to the delight of millions of moms and sexually-confused Middle School boys from Kansas and Arkansas.
Clearly everyone knew something I didn’t.
Four days later, I really ripped this pair of light blue Brooks boxers. Two minutes later, all but three pairs were in my trashcan and I was on Amazon (God bless) ordering a three-pack of Polo boxer briefs.
They showed up two days later and sliding those jeans on over them for the first time was like riding on a cloud. So comfortable. No ripping. And oh yeah, then there’s the “other” upside to them, but we don’t need to talk about that. There’s a 60% my mother might read this.
So what do I have to say to the boxers that served me so faithfully for about twenty years of my life? Honestly, I wish I had known how much more I would like boxer-briefs at least a decade ago. And as for color-coordinating them with my dress shirts, I’ll let someone else with more free time than I have worry about things like that.