This article was created in partnership with Underwear Expert
Many gay men first confronted their sexual urges in the underwear aisle of retail stores.
Ah, yes, the holy grail of masculine eye candy! What closeted teenager hasn’t blissfully lost themselves browsing packages of briefs, boxers, and plain tees, momentarily forgetting whether they were shopping for undergarments or rock-hard abs and bulging crotches?
However, proud gay men prefer to peruse hot bodies on the apps, where there’s an actual chance to sleep with them. As a result, we lose the thrill that once came with shopping for underwear. While stores might flaunt homoerotic branding, mainstream products rarely cater to queerness.
Enter Michael Kleinmann, founder and CEO of Underwear Expert, who made it his mission to create a safe space for gay underwear and related lifestyle product shopping, combining his expert requirements for quality with his immaculate taste as an LGBTQ+ tastemaker.
In an exclusive interview with So.Gay, Kleinmann recounts how his quest to help gay men feel their best reinvigorated the entire industry with diversity, created a community of underwear lovers, created National Underwear Day, and led him to the heart of gay culture.
In August 2003, New Yorkers all around Manhattan were treated to a glimpse of Kleinmann and supporters marching the streets in the name of briefs for the first National Underwear Day, a “holiday” Kleinmann created.
“We had CNN following us live on TV,” says Kleinmann. “As I was walking, I did like 20 live radio interviews and [achieved] 100 million+ impressions online.”
It all began as an SEO strategy, something very rare to do in 2003. Before founding The Underwear Expert, Kleinmann launched and led Freshpair, one of the largest underwear e-commerce platforms in that era. While brainstorming ways to drive traffic to the site, he proposed spearheading a special day for the industry, something he hoped would spark national interest. He crafted the plan for National Underwear Day to achieve specific goals for his SEO strategy.
Kleinmann was right—the buzz snowballed into a fully legitimized day. Over the years, he kept raising the bar on celebrations, including a 50-foot elevated runway show smack in Times Square, across from Good Morning America, and invite-only events with hundreds of VIP guests, and a celebrity-studded red carpet. Kleinmann appeared on numerous cable and network television shows to bring more attention to the underwear industry via National Underwear Day.
Although Kleinmann was rubbing shoulders and striking deals with renowned brands, success didn’t equal fulfillment. Marketing underwear to the masses lacked the meaning he would find in serving the community he called home.
After selling Freshpair, he was sitting in the office of a friend who served as a former Chief Creative Officer of Calvin Klein and helped create Calvin Klein Underwear, and asked him a simple question with a complicated answer: “What should I do?”
The exec pointed out that the two most influential people in men’s underwear were sitting in that room. So, quite frankly, Kleinmann was free to pursue whatever endeavor in the industry, and now with the guaranteed support of the biggest brand.
Hard nipples and well-defined bulges aside, the underwear business is historically a straight man’s game with little visibility for queer executives. And with few risk-taking for products, until Kleinmann appeared on the scene.
“There’s always been an aspirational element to buying underwear,” says Kleinmann. “You want to look like the guy in the picture.”
The homoeroticism of most undergarment packaging often reflects a projection of gayness rather than a championing of it. In 2012, Kleinmann utilized a decade’s worth of connections to bring the rainbow into focus across the sector, launching The Underwear Expert.
The company started as a blog where Kleinmann built the first ever men’s underwear editorial team and wrote thousands of articles, produced hundreds of YouTube videos, answering any and every question a gay man might have about underwear. They received hundreds of samples per month from brands wanting The Underwear Expert to review their products.
In 2015, he pivoted into a subscription-based service where customers could sign up to have a curated selection of underwear in the amount and frequency of their choosing, all based on Kleinmann’s experience. He did this by architecting and building a very complex curation software platform, which is at the very core of what makes Underwear Expert unique. “Underwear Expert’s curation platform is turning 10 years old and has evolved very considerably to meet the needs of today’s consumer” says Kleinmann.
Kleinmann recounted being in many meetings where underwear executives didn’t want their products or marketing to seem “gay,” and he turned that into an opportunity for Underwear Expert.
“I also had all of these really deep relationships with many brands big and small, so I knew what was good quality and what wasn’t,” says Kleinmann. “I wanted to focus towards the gayer brands I knew, bring on newer start up brands that I hadn’t worked with, and evolve the industry to serve our niche.”
The Underwear Expert developed a rigorous vetting process for every item in its inventory. But what truly set the company apart was how it redefined the tradition of using sex appeal to sell fabric. Featuring gay models and influencers, its homoeroticism wasn’t just implied; it was a joyous slap in the face.
Customers could still purchase briefs or boxer briefs, but they could also choose from more sultry options like jockstraps and thongs.
“Apparently I’m responsible for dozens of brands creating thongs,” says Kleinmann. “They never wanted to do that before, but I convinced all the CEOs there was a market. I also convinced all the vendors to start to make 2XL because a lot of them only did extra large.” Kleinmann laughed when he told the story that “once I was interviewed about underwear trends and I must have said the color purple was going to be hot, and then next season everyone started making purple underwear, so I knew I had to be really careful next time I was interviewed!”
Fast forward to today, The Underwear Expert has evolved into a full-fledged gay lifestyle brand; you can also find the addition of sex toys and wellness products in its inventory.
“I’ve been in the men’s underwear business for 30 years and no one has had more of an impact like Michael. Michael was a visionary turning Freshpair into a more than just a commerce site – it was the gold star for everyone in the industry to try and emulate. Michael creating National Underwear Day was pure marketing genius. Companies like mine were lining up to be a part of Michael’s plans. Evolving with the times, Michael created Underwear Expert and had the buzz of the industry. Over the years I would lean on Michael’s expertise in marketing and design. Michael has his finger on the pulse of the gay community and even helps my designers create our Pride Collections.” said Ralph Beyda, President of 2XIST.
It’s an inspiring success story of a business leader who not only climbed to the top of the underwear industry but built a ladder for gay men to follow, by following his gut and not caring what mainstream marketing dictated, or taking no for an answer.
“I’ve designed Pride collections for numerous brands and I’ve helped some of the largest brands represent Pride correctly,” says Kleinmann. “A large percentage of what we carry in our Underwear Club is made custom for The Underwear Expert by the brands themselves. We have custom colors of existing styles as well as entire collections made just for us – only because of my deep relationships over the past 2 decades. I’ve even educated the brands on how to make products that better target our niche, from fit to function. ”
Happiness might come from within, but ask any fashionista, and they’ll tell you it starts with the underwear you slip on.”Underwear is the first thing you put on and the last thing you take off but the most important thing you wear all day” says Kleinmann.
Of course, some gay men might argue the fun truly begins when another is taking it off. The Underwear Expert bridges self-love with gay love.
