I’ll second or third this. Once I realized that my ExOfficios don’t show any wear after years of use, I decided that $30 isn’t so bad when they easily outlast my cotton undies. They’re super comfortable and wick away sweat, so I’m relatively dry even when exercising.
I remember way back in boy scouts, one of the leaders was proud that he had the same waist size since he was a young man. Sure, but he wore his belt nearly down around his knees! 
A year ago or so I went from boxers under pants/briefs under shorts to boxer briefs. My wife bought a set of 3 Calvin Kleins. Must’ve been on sale wherever she was shopping. They fit well so I bought 9 more of them. They’ve held up just fine. No complaints.
I kind of enjoy the hybridized implication of the “boxer briefs” term, though. “Half boxers, half briefs—[okay that suggests a chimeric form that’s boxer-style on one buttock/thigh and briefs-style on the other, but just stay with me here]—it’s: boxer briefs!”
“What the hell is that, tobacco?” - If you know, you know.
Anyway, I’m a big fan of boxer briefs for sleeping in, so as the elastic looses it’s oomph over the years, those pairs get relegated to “sleep only” use. I think it might be worthwhile for @craft458 to mention what brand they’re already using so we can rule it out, as well as similar products.
It might be nice to know material preferences as well. I’m fond of old school fabric options, but I got a 4 pack of Spyder’s as a gift, and while they were indeed extra breathable and wonderful on hot days, they fail in colder weather and can be actually slippery when you’re not wearing anything else.
I’ve always just bought boxers at Target. I’ve not noticed them to be difficult to find. I’m checking the website now and my local Target has a 7-pack of Fruit of the Loom plaid boxers (not boxer briefs) for $14.99.
In-store, my Target had a huge selection, like 30-40 different sets (packs) of boxers, briefs, boxer-briefs, and everything in between, from multiple vendors.
But the store was severely under-staffed, and the merchandise was disorganized and haphazardly placed across several nearby stands, with duplicates and misplaced items everywhere. This was in 2025, not during COVID, mind you. It was a pretty bad shopping experience. It was actively painful to find my size, because the same style/model of boxers would have its colors & sizes spread across several different stands, with no rhyme or reason.
Maybe it’s better online, but yeesh, what the hell happened to Target… it used to be the place that cost a little more, but not too much, while still providing a nice experience. Now it’s just a mess.
Do you find this true at all locations by you? Maybe it’s just your particular store or area. I’ve not noticed my Target or any nearby ones to be particularly disorganized and it’s like shopping at Saks Fifth Avenue compared to Walmart.
There is only the one near me, so I have no points of comparison.
I hope you’re right! I rather like(d) Target, and was sad to see it succumb into ruin like this. The boxers section (and clothing overall) felt rather… apocalyptic. Hopefully it’s just this one store. (edit: though the internet shares my concerns, it seems… 1, 2, 3, 4, 5, etc. But that’s enough of a hijack.)
The multiple Targets near me have distinctly different feels.
But in each case it seems the customers utterly trash the displays by mixing stuff up, and there’s very little staff effort expended keeping up with that mess. And any resemblance between what their website says in in stock at a given location and what’s actually there is entirely random.
I suspect these two issues are related.