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Welcome to the Esquire Endorsement. Heavily researched. Thoroughly vetted. These picks are the best way to spend your hard-earned cash.
I used to take underwear as seriously as the next guy. Which is to say I would go to Target every six to 12 months and pick whatever was on sale and fit me. It works, sure, but every shopping trip is a struggle to remember what I like and which generic or licensed clothing brands make underwear that’s actually good. I was never a guy with a go-to pair of underwear. All it took to change that was a pair of Calvin Klein boxer briefs. Now I realize I never needed to get more “serious” about my underwear at all. What I needed was a seriously comfortable pair I could keep going back to every time I needed more.
That’s exactly what these are. Of course, the marketing machine made Calvin Klein underwear a status symbol, but there’s more to it than giant billboards with hot guys’ abs and bulges. I’m not reordering Calvins because I think I’ll look like Jeremy Allen White. (Though maybe they give me a little more A-list confidence.) I’m reordering Calvins because I’m getting a solid pair of no-frills, 100-percent-cotton boxer briefs with a simple elastic waistband. That’s what has actually made these an indelible classic. Plus, you can find them anywhere. I can order from Amazon, or any other online retailer I prefer, and a brand-new three-pack will be on my doorstep before laundry day.
Shop $39, amazon.com or nordstrom.com
Soft and Snug
I’ve always been a boxer-briefs guy. I know the laundry list of issues guys can have: bunching, chafing, elastic marks from too-tight bands. I’ve experienced it all in my 30 years on this earth, the kind of daily discomforts that you get used to until you realize a pair of underwear that fits right doesn’t do these things.
The classic cotton boxer briefs from Calvin Klein aren’t just hassle-free; they are supremely comfortable. I have plenty of space down there (room to breathe, if you will) but with all the snug structure I go to boxer briefs for. Nothing hanging loose like with a freewheeling pair of boxers. Same goes for the elastic, which hits that perfect comfort level—staying up effortlessly while never feeling too tight. Perfectly breathable and great for an everyday level of physical activity, even in the humid 80 degree dog days of early summer.
Shop $39, amazon.com or nordstrom.com
Classic Style, No Frills
I spend a lot of time writing about tech and gadgets that are trying to “disrupt” their respective industries. This extends to the closet, where I have underwear for travel and sporty mesh pairs made for my most active days. Yet during my recent world travels (I’ve been to Italy and Korea in the past month), I didn’t take any of those with me. I instead packed all three pairs of my Calvin Kleins.
These boxer briefs are the definition of tried-and-true. Hell, after trying them even I had to admit that every word of glowing praise I’d ever heard about ’em was true. Let me put it this way: Now when I open my underwear drawer, this is the pair I reach for. If all my Calvins are in the hamper, I know I’m in for a tough day.
Shop $39, amazon.com or nordstrom.com
Affordable and Comfortable, Every Time
I understand Calvin Klein boxers aren’t as affordable as other options out there. Let’s look at it this way: A good pair of boxer briefs will last you upwards of a year, two if you have a deep rotation and don’t wear them regularly. This isn’t a forever purchase, but you can get more use out of a higher-quality pair of briefs. This is more of a “keep these bookmarked in your order history” situation, so that the next time you go to buy underwear, you’ll know exactly which ones to get again. Even better, set these babies up to auto-ship every 12 to 18 months and you’re golden. Rotate out the oldest pairs every year. A lifetime of boxer-brief bliss for less than $50 a year. In this economy that’s as good as it gets.
Trust us: The classic style will never get old, and we have yet to find fancy, “innovative” boxer briefs that are more comfortable than this. No, we’re pretty sure Calvin Klein has underwear down to a science, and these, my dear reader, are the perfect specimen.
Shop $39, amazon.com or nordstrom.com
Photographs by Florence Sullivan
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