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Michael Kleinmann's journey to expertise began in 2001 with the launch of Freshpair. From a bedroom office in New York City, he pioneered online shopping for underwear and catapulted the industry into the 21st century, giving the old guard of department-store retail a run for its money. But he didn’t just sell underwear, he put it at the heart of popular culture. Heard of National Underwear Day? Michael invented it, because he believed underwear deserved its day in the spotlight. Five years later, Freshpair was flourishing, with more than 30,000 SKUs from over 100 brands, 8-figure revenue, and was one of the largest sellers of nearly every brand imaginable. Michael had reshaped the industry forever.

With Freshpair a resounding success, Michael was ready for his next challenge: Underwear Expert. It launched as a digital media brand that would deep dive into the men’s underwear industry in a way no one ever had. He published underwear reviews, trend stories, shopping guides, produced hundreds of photo and video shoots, and created over 8000 unique articles. Underwear Expert quickly emerged as the industry thought-leader. In turn, brands eagerly sent Michael underwear by the truckload, eager to have their product featured and reviewed by the expert himself. Michael could tell when a tag was going to scratch you, when the leg openings were cut too small, when the pouch wasn’t shaped right, when the seams were going to annoy you by lunchtime — all from picking up a pair and just looking. Brands recognized his sixth sense for underwear, took his feedback to heart and redesigned. He emerged as the true underwear authority.

In 2015, Michael transformed Underwear Expert into what it is now: an online subscription service selling handpicked brands from around the world — leveraging over two decades of experience to curate unique selections for men based on their personal size, fit, and style preferences — all filtered through his savant-level expertise. The guesswork in finding great underwear is now a thing of the past. Thanks to Underwear Expert, men can enjoy “that best pair feeling,” as Michael likes to call it, with every pair.