Ever wondered what exactly to look out for—aside from recognizable brand names—when buying men’s underwear? The Queer Review’s editor James Kleinmann speaks with his long-lost cousin (probably) Michael Kleinmann, the Founder and CEO of Underwear Expert, to find out. Initially an influential digital media brand, in 2015 Michael transformed Underwear Expert into a leading underwear subscription service, leveraging over two decades of experience in the business and smart tech to offer a curated selection for his customers—mostly gay men—based on their personal style, fit, and size preferences. Alongside the impressive array of briefs, boxers, jockstraps, and thongs on offer, you can also pick up some handy grooming products, lube, dietary supplements, adult toys, and more while you get your perfect pair of underwear.
James Kleinmann, The Queer Review: What sparked your interest in underwear as a career and how did you became the underwear expert?
“I’d never even thought about the category at all before I got involved in a business that was selling underwear that I wound up taking over and turning into a very large company over 10 years. We sold both men’s and women’s underwear and had 150 different brands. Back then, I created National Underwear Day which got tremendous exposure. After that experience I became really well-known in the business as ‘the underwear expert’.”
“When I eventually sold that company, I wanted to stay in the industry because I knew so much about it and as everyone was already calling me ‘the underwear expert’ I thought why not create a company called Underwear Expert! For the last 10 years, I’ve been running Underwear Expert, originally as a content marketing site, and then eventually we evolved into a subscription box.”
Why do you think men’s underwear is a garment of clothing that’s worth giving our attention to?
“For a really long time women’s underwear had a lot of attention and men’s underwear didn’t. Then over time it evolved and at some point men’s underwear became more of a mainstream topic. Now it’s socially acceptable to talk about as culture has shifted.”
What kind of impact has social media had on men’s underwear as a business?
“I wish social media had started 10 years earlier when I would do National Underwear Day in the middle of Times Square. A few years ago when influencer marketing started, brands were able to use social media to get attention whereas prior to that they would’ve had to sell their product to a large retailer. So we saw all these tiny companies pop up from nowhere using social media to grow their businesses. Essentially, the barrier to entry in the industry completely shifted with the Internet and then again with social media. Underwear models now even have their own brands because once they have a certain size following they try to monetize that and underwear happens to be a good category.”
What are the some of the things that you would recommend people to look out for when they’re buying underwear?
“With men’s underwear specifically there’s a lot of stuff out there that is low quality and just because they have great marketing doesn’t mean that it’s a great product. So you really have to try things out and see for yourself if you like it because everyone has their own personal style. The most important thing is that it’s comfortable and that can mean different things to different people. Fabric is extremely important and so is the way it fits. So try different things to see what you like and then you can buy multiple pairs of that brand.”
What are your own personal preferences when it comes to underwear?
“I have to be careful with my opinion on best brands and what I wear because someone once asked me this question and I said something about purple underwear, then all of these brands started making purple underwear! Generally speaking, I like trunks. A trunk is a boxer brief that’s a little shorter. So it might have a one or two-inch leg instead of a three to four-inch leg. I like those because they don’t ride up and I can wear them daytime or nighttime. I could wear it to the gym or just lounging around. They’re very versatile. When I was younger I used to wear briefs, then I feel like I grew up and started wearing trunks!”
I wear briefs but they can be quite hard to find in stores.
“Our customer base is 85% gay men and our top selling style is briefs. If you go to other stores or online retailers they’ll have completely different metrics than we do, but briefs are number one for us, then trunks, then jockstraps, then boxer briefs, and then thongs.”
It seems like thongs have become popular with men over the last couple of years.
“I don’t think thongs have become more popular, it’s just easier to find them. I’ve changed underwear trends a lot over the years and I’ve convinced dozens of companies to make thongs, so you might be seeing them more because they’re making them now. There was always a certain demand for them, but I don’t think that’s changed significantly. Also, it’s perfect for the Internet because a lot of men don’t want to go into a store to buy a thong.”
Are there any current men’s underwear trends that you’ve noticed or that you’re particularly excited by?
“There are only so many ways that you can make a pair of underwear, it’s not like a car, you can’t really change it that much. But what you can change is fabric, colour, and print. Fabric has had the most innovation over the last decade and there are so many choices out there now in terms of different blends of fabric with different moisture wicking and other properties. It’s not like before where you only had two choices—either it was 100% cotton or some kind of synthetic option—now there are a zillion different options.”
What are some of the things that you considered when you were creating Underwear Expert’s subscription service?
“Previously I operated an online store where you could buy a one-off item, but I wanted to do something different this time because I thought that was kind of boring. So I put together this idea for a subscription. Being the expert, I wanted to offer as much as I could to the customer so that the subscription could be as perfectly tailored to them as possible. A lot of times with subscriptions you get stuff that you don’t like for whatever reason or that’s not right for you. Underwear happens to be a garment that’s very personal, people have very specific things that they like or don’t like, so there really couldn’t be a one-size-fits-all underwear club. It had to be as personalized as possible.”
“I took my background in technology and we built some software that could help us to curate underwear for our customers based on my 20 years experience in the business. We have 50 different brands and about one thousand different products at any one time that we curate from. So you go to the Underwear Expert website and tell us your size and what you like—the styles, briefs or trunks, the colors you like and don’t like—and then we take all that information and figure out what would best fit you as a customer. Then we show you what we’ve come up with and offer you alternatives, because maybe you don’t like the shade of blue that we picked out and you want something different, so we let you preview and refine your order.”
“We built some sizing technology because every brand size is different and a medium in one brand is not a medium in another brand. So we ask you for your waist size and then we take that and we convert it to the size in the brand that we’re going to send you. That ensures that you’re always getting something that’s going to fit. We try to think about all the different things that happen when you’re dealing with a multi-brand curation system and we’ve built a large amount of technology that makes it easier and ultimately better for the customer.”
“We also sell products other than underwear, so you can add something else to your box if you want and then we ship it out to you. You don’t need underwear every month and often with subscription programs you get too much stuff, so we let you get your underwear whenever you want it, whether it’s every three months or every six months for instance, and you can also change the quantity.”
You mentioned that 85% of your clientele is gay men, what’s the significance for you of Underwear Expert being LGBTQ+ owned and run, how does that shape and affect the business?
“It didn’t start out as a business targeting gay men, it started out as a business where we were curating all the underwear that I thought was great. When we started asking our customers for information about who they are, and also from looking at what people were buying, we realized that they were mostly gay men and we honed in on that. Being part of this customer base myself, it just made a lot of sense to me to specialize in this. We can’t be everything to everyone and there are a lot of brands out there that are not targeting this niche or if they are it’s as an afterthought. Being part of the community, I want to create something that’s a safe space for buying underwear and other things of interest to gay men.”
Wearing my favourite underwear makes me feel good about myself, even if no one else gets to see it that day! Do you get some nice feedback from your customers?
“Yeah, we get detailed feedback from people, you’d be surprised! A long time ago I said that underwear is the first thing you put on and the last thing you take off, but the most important thing you wear all day. I think that still holds true because there’s nothing like the feeling of a new pair of underwear. You may not think about it during the daytime, but if it doesn’t fit well then you definitely will think about it. It’s something that supports you and takes you through your day. If you’re wearing something that’s fun, only you know about it and that’s a little thing that you can carry through your day.”
By James Kleinmann
Find your perfect pair at Underwear Expert and follow Underwear Expert on Instagram, TikTok, YouTube, Facebook, and X. Take Underwear Expert’s fun Am I Gay? Quiz [Editor’s note: I only scored 73%, must do better next time].
Watch the full interview here: