What’s in Your Drawers Matters: The Underwear Expert

Most men think they can get away with wearing the same pair of underwear until it falls apart. This might be cost efficient but it won't help you in the bedroom department. Nothing is more of a turn off than when a guy takes off his pants and he is wearing terrible, ill fitting, hole-ridden underwear. That's right, it's not just women who have to care about wearing attractive underwear anymore. Luckily, none of those men are readers of Addicted, right? We know better. So to make your life easier, we have sourced the best way to ensure you always have a good pair. It's easy. Just sign up for an underwear subscription. And the best in the business is The Underwear Expert.
The company was started by Michael Kleinmann who wanted to make shopping for your skivvies easier and more comfortable. So who better to give expert advice on the subject than the man himself. We sat down with Michael to learn more about the latest in men’s underwear and why you should trust him.

A: First off, why should we all consider you the expert?


MK: Great question. I was the President of a very large online underwear retailer called Freshpair, which started out of my apartment and I built it to be a leading underwear retailer when I was at the helm – and sold it after 10 years. In 2003, during my tenure at my former company, I created National Underwear Day which is now celebrated worldwide. My experience during those 10 years led me to found a new company, The Underwear Expert, which originally started as an informational site covering everything happening in the men’s underwear universe.  We wrote thousands of articles since we launched, created content for Menshealth.com  and syndicated our expert content to other publications. The NY Times has quoted me several times on the topic of men’s underwear  and I am in touch with hundreds of men’s underwear companies on a regular basis to discuss trends and where the industry is headed. I don’t remember where the name came from but someone called me “The Underwear Expert” a long time ago and I decided it would be a great name for my new company.


A: What have you noticed in all your years in the business? What are the trends you seem to be seeing?


MK: In the past 15 years that I’ve been in the industry, I’ve seen men’s underwear evolve from an unmentionable to a fashion item. It has evolved from basic styles to colors that follow fashion trends. Brands produce such a wide array of colours and prints now that underwear is no longer boring. I’ve also seen the rise go from mid to low as pants became more fitted and had lower rises. Another innovation is in the fabric – brands are doing a lot with fabric recently.


A: The men’s underwear market is very crowded with so many new brands. How do you decide what makes in into your selection? Any recent finds that are your favourites?


MK:For our Curated Underwear Club, I personally wear test every pair we let into the club. I want to personally see each pair so I can make sure it is up to my standards. As much as the colors and design of the underwear are important, I also pay attention to fit and fabric. If the tag is irritating, or the legs are too tight, or there’s something else that is off, I call the owner of the brand and ask them to fix the product if they’d like to do business with us – and in many cases, they do.




A: In the dichotomous world of boxers or briefs – do you find men still stick to one or the other?


MK: Boxers are old school. They have a time and place and I think fashion conscious men have moved way beyond boxers.
Our youtube videos with our weekly “boxers or briefs” videos are very popular but not because people are wearing boxers. There are more flattering, functional, modern styles that guys should be wearing. Currently, our underwear club carries boxer briefs, briefs, trunks, and jock straps. Our customer is more fashion savvy, so the most popular styles (in order) are briefs, trunks, jock straps and boxer briefs. With a more mainstream department store customer, Boxer Briefs and Briefs are the most popular with trunks following and jock straps a very small portion if they even carry them.


A: A lot of men like to stick to their comfort zone – especially when it comes to underwear. Any suggestions on how or why we should step out of the box?


MK: When I launched the Curated Underwear Club, I was shocked by how many guys wrote in comments about how they would never have picked out the items we sent them but after trying them on, they felt very comfortable wearing new styles and some colour. Underwear purchasing can be intimidating with the hundreds of brands out there and nobody is making sense of the category in an intelligent way. We make it easy for guys to stay within their comfort zone. But have us pick out items that they would never have bought themselves. Our site allows guys to choose their styles (briefs, boxer briefs, trunks, jocks) and answers some other questions about taste level, colour and size, and our advanced technology and an amazing team does the rest. Its easy and guys love the process.


A: Any last words?
MK:Sometimes you don’t know you need something until you try it. Better underwear is one of those things.


The Underwear Expert is definitely the go-to service all men should be using.  The site is very easy to navigate. New users take a quick survey that not only includes their exact size (done in inches or cm as all underwear fits differently). But they also ask some lifestyle questions like colour preference, sporty vs classic, etc. And they do it all through pictures. Super easy and you will end up with underwear that fits. Moreover, unlike other services we tried, you get pairs you will actually wear. And you will discover new brands.They have also added a new preview feature so you can swap out your upcoming shipment in case you don’t like what they have picked for you. You can subscribe to receive anywhere from 1 to 3 pairs per month or every 2 or 3 months. You can opt for briefs, boxer briefs, trunks or jockstraps. Rates start at $24 USD. We tried the service and loved it. But don’t just trust us, trust the expert.

One final note, take care of your drawers.

Christian Dare
Christian Dare spent much of his formative years working in the fashion industry as a National Visual Manager before he turned his attention to writing. He currently writes for AmongMen, Complex and his own blog, Christian Dare Edited. You can find him online at www.christiandareedited.com or follow him on Twitter @christiandare but he is more fun on Instagram @christian_dare
Christian Dare