I am on an underwear kick right now. I can’t help it. I have been reevaluating my underwear drawer since I had my conversation with David Ehrenberg, the CEO of Pair of Thieves, earlier this week. I mean, how often do men think about their underwear? The truth is, while we don’t think about it often (hopefully you are a little bit after reading my last article with David), I have discovered we actually DO think about it in some ways. We just need to change how we think about it. Ladies, go ahead, ask your guy what underwear he is wearing right now. There will be two answers. 1 – “No clue, what did you buy me?” 2 – “My favorites.” We’re weird about it. We all have at least one pair we wear all the time. It is our favorite pair. Then we have the others, the ones that are just the day-to-day. And finally, we have the ones we never want to wear, but it’s a laundry emergency, so we must. In all likelihood, this pair has been with us since Mom bought them for us. That’s right, yeeeeeeeears ago.
Fellas, it’s gross. I often think about a movie quote from Smokin’ Aces, by the always-great Jeremy Piven. “There is not a laundry detergent or dry cleaning product known to man that will get that out. Suffice it to say, some sh*t, don’t wash out.” There is a moment in time when your underwear is done for, beyond saving. But, when do you know when to give up on old faithful? David and I hashed it out.
I think it starts with changing how people think about underwear in the first place. A lot of guys are still wearing the same styles they wore years ago– sometimes because it’s what their mom used to buy, sometimes because they’ve never gotten around to updating it, and sometimes because they just don’t think underwear is worth paying attention to. – David Ehrenberg, CEO, Pair of Thieves
When was the last time you thought about underwear?
It was always mindless for me, so no judgment. I went from my mother buying me whatever was convenient at Walmart or Target to the United States Army giving me whatever I needed to stay alive. Then, when I was out on my own, I just wore whatever I could get my hands on. I would be out of underwear one day and buy more. Or I would keep washing and rewashing the ones I liked. When was the last time you evaluated your own underwear drawer? Well, it is high time we do that.
“The reality is, underwear is one of the few things you wear every single day, yet it’s often the most overlooked part of a wardrobe. We update our phones, our sneakers, our workout gear, even our mattresses, but many guys haven’t reconsidered their underwear in years. We’d love to get more people to realize that better underwear does actually exist, and that they deserve something that feels better, fits better, and works better for the life they’re living today– not the life they were living ten years ago. It’s less about throwing something away and more about giving yourself permission to upgrade something you use every day.”
How long do your skivvies last?
I mean, this can’t be a hard and fast answer, right? It has to be a mix of so many things. But the hard and fast rule in my head has to be that taking care of things makes everything last longer, right? Of course, for underwear, it must come down to washing it. Every wear, duh. But with many articles of clothing, frequent washing breaks them down. So, what is the underwear’s expiration date? Why isn’t it stamped on there? Can we get a wear counter on the tab? Where is an engineer when you need one? How long do these actually last?
“There’s no hard-and-fast expiration date for underwear– it depends on how often you wear it, wash it, and what condition it’s in. The bigger issue is that most guys keep pairs in rotation long after they’re delivering the comfort, support, and fit they were designed to provide. Underwear is one of those categories where the decline happens gradually. Fabrics lose recovery, waistbands stretch out, and moisture-wicking or performance features simply aren’t working the same way they did when the pair was new. Because it happens little by little, most people don’t notice the difference. We’d actually encourage guys to think less about a specific replacement timeline and more about whether they’re still getting the experience they want from what’s in their drawer. If you’re constantly reaching past certain pairs, that’s usually a sign. The other thing that’s changed is the product itself. Underwear has come a long way over the last decade, with major improvements in fabric technology, fit, breathability, and comfort. A lot of men are still wearing the same styles they’ve always worn, not realizing how much better the category has become. At the end of the day, underwear is the first thing you put on and the foundation for everything else you wear. It’s worth giving that part of your wardrobe a refresh every once in a while– not just because older pairs wear out, but because newer ones can genuinely make getting dressed more comfortable.”
Proper care means I can wear them longer, though, right?
I will definitely get stuck on this. The conversation around how long underwear will last kept coming back to taking proper care to extend the shelf life of my unmentionables. I have always been the kind of guy who saves clothing until I absolutely HAVE to get rid of it. I hate the fast fashion trends of the last decade, and I will always lean towards long-lived garments. However, I had never thought about the primary function of underwear. David had to walk me back from the edge of a brain melt when I was thinking about the amount of underwear I would need to ditch because I bought them back during the housing crisis of 2008.
“Sure, proper care helps. Washing responsibly, avoiding excessive heat, and rotating your pairs will all extend the life of your underwear. But the bigger question is: why are we so focused on making underwear last as long as possible? Think about running shoes. You can keep wearing them long after their peak, but eventually the cushioning and performance just aren’t there anymore. Underwear is similar. Over time, fabrics lose recovery, waistbands relax, and support changes– even if the pair still looks fine. So yes, take care of your underwear. But we’d argue the goal isn’t to squeeze every last day out of it. It’s to make sure you’re still getting the comfort, fit, and performance you want from something you wear every single day. What we focus on at Pair of Thieves is making sure that “good life” is as long as possible from the start– better materials, better construction, better recovery.”
Ok, fair, I’m convinced, how do I build an underwear wardrobe?
That is right, I said an underwear wardrobe. I am making that a thing. Go ahead, mark this date down. In about three months, the TikTok explosion of the “underwear wardrobe” will take over. Just remember that you heard it here first. But seriously, have you ever thought about building a wardrobe full of the best underwear to fit your lifestyle? I hadn’t, until David helped me wrap my mind around it.
“I’d keep it simple. First step: clear out anything that’s seen better days– no sentimental attachment to stretched-out pairs that have run their course. Then rebuild with some intention: a core set of everyday pairs you actually like wearing, not just tolerate. For us, the best underwear is ready for anything your day throws at you– work, workouts, travel, weekends, all of it. That’s always been part of our DNA. From there, it’s about personal preference. Maybe you like different fabrics or silhouettes, but the foundation should be a drawer full of pairs you can reach for without thinking twice. The goal is simple: every pair in your drawer is one you actually want to wear.”
There it is. I guess I have to lose the sentimentality of my Army skivvies, and I think Mom will forgive me if I throw away a pair of underwear she bought me for Christmas before Home Alone 2 came to theaters.
