I talk a lot about the importance of style. Fit, function, and fashion come together to make your personal appearance a reflection of who you are and who you intend to be. The value of quality over brand names. The importance of good tailoring over fast fashion. Wearing a suit the right way. The best shoes for your look. The way you can send a message without ever opening your mouth. But you know what I don’t ever talk about? Skivvies. That’s right, I don’t talk about underwear. You know why? Because it is something that I (and I reckon you too) just don’t think about. But, in ten minutes with David Ehrenberg, CEO of Pair of Thieves, that all changed. I started thinking about underwear. And he convinced me to try his brand, because he was certain that my balls would love it. He was right. But what is it about Pair of Thieves, and underwear in general, that made them skyrocket to the top of an industry most men don’t think about?
Our goal isn’t to make underwear some aspirational luxury item– it’s to make it the best part of getting dressed. That’s reflected in our fabric, our fit, and how closely we listen to real customer feedback. We see underwear as part of personal care, and upgrading it should feel easy, accessible, and genuinely worth it. – David Ehrenberg CEO Pair of Thieves
The biggest brand you’ve never heard of
When they say they are the “biggest brand I have never heard of,” I had to dig in further about that. I wanted to know what they meant, how they qualified that statement. And, it was crazy to find out that Pair of Thieves, a brand I indeed had never heard of, was the third largest underwear brand on the market. The two above them, you have almost definitely heard of. But, how did they do it? How did they grow to that size without bringing a recognizable name with the journey?
“We say it pretty directly,” Ehrenberg says. “Pair of Thieves has grown into a major player in men’s essentials, but we don’t always have the name recognition people expect for a brand at our scale. A lot of that comes from the path we took. We weren’t built on decades of legacy or traditional wholesale dominance. We grew through product obsession, digital channels, and retail partners who took a chance on us early. Today, we’re available online and in more than 6,000 retail locations across the country, making the brand incredibly easy to discover and shop. We’ve always believed the best marketing is a great product that people actually want to wear. It was pretty simple: make something better, let people find it, wear it, and come back for more. So while we may still be introducing ourselves in some rooms, we’re already in a lot of drawers.”
Why underwear?
Ok, let’s be honest, you likely don’t have any idea what brand of underwear you’re wearing. Go ahead, take a look, I bet you’ll be surprised by the brand. The truth is, we go from mom to girlfriend to fiancée to wife who dresses us the way they tell us looks good in most cases. That is something I am attacking at every turn as often as I can. But, in all of those aspects, the last thing we buy for ourselves is underwear. It is likely bought at the same time and in the same store that your partner picks up the bread and milk. So, what possesses a man to dedicate his life to draping men’s nether regions with a superior product? I mean, when I met David, and I heard how passionate he is about underwear, I had to ask the one question plaguing me through the entire interview: Why underwear??
“Pretty funny– this is a question we get a lot,” Ehrenberg chuckles. “My co-founders and I didn’t set out thinking we were going to build an underwear brand. We actually started with socks. We just weren’t that excited about what was out there and thought, ‘we can make something better.’ That same thinking carried into underwear. We kept coming back to the same thing– guys were kind of just tolerating their underwear. It was uncomfortable, boring, overpriced, or some mix of all three…. And this felt like a weird gap in something people wear every single day, so we set out to make a product guys would actually want to wear. Once we started designing and testing, we found ourselves digging deeper into every detail—fit, fabric, movement, temperature regulation, durability, even how different guys want their underwear to feel and function. The more we refined it, the more focused we became on getting every element right. At a certain point, it stopped being just another product and became a challenge we were genuinely obsessed with solving.”
Is underwear just underwear?
Do you really care? If you have read this far into the article, then you care a little, right? Maybe you are also fascinated by the idea that a man could be passionate about underwear. But, then again, shouldn’t we all care about the underwear cradling our constant companions? I think so now, but it took someone like David to ignite the idea. So, how do you get men to care about underwear?
“You’re right,” Ehrenberg admits. “The thing is, you can’t really change that mindset with messaging; you have to change it with experience. The moment someone tries a pair that doesn’t ride up, doesn’t bunch, stays cool, and actually feels better at 6 pm than it did at 8 am, the mindset shifts pretty quickly. There’s not much to debate after that. There can be a tendency to treat underwear as an afterthought, so we’ve always focused on delivering a product that feels like an upgrade without making it feel like a big commitment. We keep the price approachable and the barrier to trying it low. Once people wear it, the difference tends to speak for itself. So really, our job is pretty simple: get the product on people in a way that feels easy to say yes to. Humor, branding, and accessibility help get attention, but retention comes from performance. Once a guy feels the difference, ‘underwear is underwear’ stops being true.”
David and I are in agreement on one very big thing when it comes to underwear: “If something’s going to be on your body all day, every day, it should probably be great. That’s basically how we think about it.”
