July 23, 2017
advice articles
A Firsthand Men’s Underwear Guide

A Firsthand Men’s Underwear Guide

There are a lot of questions I get asked pretty commonly. How long have Will and I been together? Who tops and who bottoms? How does someone come out? How big is my dick? It pretty much comes with the territory of putting tidbits of your personal life online, I suppose. Although there is one question I get all the time that I haven’t really been able to fully answer, until now. A lot of you guys know that I used to work for a certain men’s underwear company (and that we parted ways on not-so-good terms). I assume that’s why I get a lot of questions like this in my Tumblr inbox.

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An excellent question. I must admit, I’ve been a little bit of an undie aficionado long before I came out, and I’ve experimented with quite a few brands, fads, fabrics, styles, and so-called “technologies”. So here are a few things I’ve learned through the years, my personal men’s underwear guide if you will…

First, you have to think about what you’re buying a particular pair of skivvs for. Are you buying them to look cute? Are you buying them because you need something to wear to the gym? Are you looking for something comfortable to wear all day while you work? What you’re looking for is going to hopefully depend on what you need. Think about it. You don’t buy only one kind of shirt and attempt to wear it for any and all occasions. You have your casual shirts. You have your work shirts. You have your formal shirts. You have your cute shirts that you’d want to wear on a date. Also, everyone’s body is different, so what works for someone with a big ol’ booty and an average size package may not work for someone who looks more modest in the back but is packing heat up front. That’s why I’ve always been hesitant to recommend certain underwear brands, since what works for me may not necessarily work for other people. For instance, I love Armani underwear. It’s always been one of my favorite ways to pamper myself in a way that’s just for me. But that being said, I one of my other friends who has a lot more junk in the trunk steers clear of a lot of Armani, because their briefs are certainly not ready for his jelly. Okay, so what if my “friend” is Will? Point is, every guy is different, so every guy is going to have a different preference.


Luckily, a lot of brands out there are catching wise and introducing underwear collections with different anatomical variations for different body types and different preferences. One such brand is Obviously, who decided to introduce four different types of pouches for their new collection. On the one hand, you have the “Classic Pouch” which creates a more streamlined profile. On the other, you have the “Anatomical Pouch”, which provides a generous amount of room up front for everything to kind of hang free. Will and I were sent two pairs of their stuff a few months back (and I’m just now getting around to this post…sorry guys). Will opted for their “Comfort Pouch” while I opted for the “Contour Pouch”. All their different pouches are made with the same soft and light fabric and have a sporty look to them. Personally, I love wearing my pair to the gym, since the pouch keeps everything in place without squashing. They’re also pretty breathable, which helps fight against swamp ass. Will, on the other hand, likes everything to fit snug when he runs, since there’s not as much jostling around. Again, different fits for different guys. It’s one of the reasons why I really appreciate that Obviously doesn’t try to take a “one fit for all” approach.

tighty whitiesBut again, that’s just one scenario. Other times, Will doesn’t mind showing a little butt cheek (especially if it’s for me). Other times, I want something more elegant and streamlined. The trick is to find that handful of brands that suit your needs and your tastes. Luckily, there are sites like Men’s Underwear Store and Freshpair that offer a very wide selection of brands and styles. These sites will also give you info on how to size each brand, since they’re all just a little bit different. Also keep in mind what you’re buying the underwear for, and keep that in mind when you look at the fabric content. If you’re buying gym underwear, you likely want something breathable and/or moisture-wicking. If you’re buying more for style and/or luxury, then you’ll likely opt for something with a more luxurious feel (microfiber…hint, hint). And if you don’t know anything about fabrics, just read the product description. The whole point of it is to sell you, and they’re most certainly going to say something about what makes the fabric so awesome.

And if you’re on a limited budget, know that all underwear sites, be they retailers or the actual manufacturers, have sales. All of them. It’s never a matter of “if”…it’s a matter of “when”. So if you’re browsing through a site and everything you like is out of your price range, just sign up for their email list. At some point, they’re going to send you an email with a coupon code or that tells you about their end-of-season clearance sale. It’s practically a guarantee.

And if you’re the kind of person who has trouble justifying paying more than $5 for a three pack of briefs, then know this. There’s certainly no requirement that everyone wear cute and luxurious underwear, and if you’re fine with your Fruit of the Looms, then screw what anyone else thinks. It’s all eventually coming off anyway. But I’ve found that, out of all the clothing items to “splurge” on, underwear is the one thing that’s truly for you. You don’t buy a bitching leather jacket just for you. You do it because you want people to see you wearing it in public and take notice. Underwear is a different story. That’s the one part of your outfit that only you know about (and maybe one other lucky guy/girl). It’s your own personal form of pampering. It’s that “secret ingredient” to your look that no one really knows about. It adds that extra bit of swagger to your step when you’re wearing an outfit that’s on point. It’s that extra bit of comfort that compliments a lazy day on the couch. And if you’re like me with cameras always rolling around the house, it’s comforting to know that I can still look cute if I get caught with my pants down.

Point is, men’s underwear has come a long way from the tighty-whitey days of yore. There’s basically been a renaissance, with more styles, cuts, colors, fabrics, and options than ever before. So why not take advantage and pamper your junk a little?

About RJ

RJ is a blogger/vlogger/writer and the other half of the NotAdamandSteve duo. When he's not making videos or writing stuff online he's usually working out, traveling, telling you factoids you never asked for, working out, or spending quality time with his new husband and German Shepherd.


  1. I like you guys always introducing us so many different cool things!

  2. I’ve been thinking about trying Obviously for awhile now; I like that they offer a lot of different lengths for their boxer-styles. And as you said the different pouches are important. I tend to prefer the anatomical pouch style but for running? Not unless I want a bruised testicle…

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