When it comes to underwear, most well-endowed men feel slighted and disadvantaged by the choices they think they must settle on, and for the most part this is the product of the same concept that the majority of men, regardless of their penis size: They just don’t know enough about the options available to them in 2013.
I was like most of these well endowed men, wearing boxers and boxer briefs that were one to two sizes too big in the waist so my bulge wouldn’t cause the legs to fit too tightly (I am not going to even mention basic briefs and our problems with those). But once I discovered the innovation of a trunk with a contoured pouch, my quest for finding underwear that fit me and my endowment comfortably began to take shape.
There are few articles out there relating to us well-endowed portion of the population, and the most prominent one currently available offers good advice, but I don’t think it goes far enough. So I have decided to come up with the best advice I can think of, based on my three-plus years of searching for the kind of underwear meant for guys like us, using pictures from my own collection as well as brand suggestions to help you get into the right pairs.
Tip #1 – It’s The Pouch, Stupid…
If you’re well endowed, the largest problem you experience with run-of-the-mill brands is they aren’t designed to put your equipment anywhere. Just as a handgun needs a holster to be carried safely, we “showers” need a place to carry our dangerous weapon. This means, the only underwear you should be buying feature a pouch that is visible to the naked eye before you put your hands on them.
Sure, some “experts” would suggest making sure the size is right on any pair of underwear with a contoured pouch, but I view this as advice that discounts your ability to think. Just know this, if you are hung, you better be damn sure the underwear you’re looking at has a pouch before you look at whether or not they have your size.
Your Best Options and My Favorite Pouch
It’s 2013, and just about every designer offers at least a few designs that feature a contoured pouch but not all of them are great for men with larger packages, so if all else fails, consider the following designs from prominent labels in men’s underwear which I myself routinely employ:
2(x)ist TOUCH Ultra Contour Briefs or Trunks (Or any other “Ultra Contour” piece they offer), on 2xist.com some older designs are still available that feature even better pouches.
Andrew Christian Almost Naked, NanoFit, Color Vibe, Air Sculpt, Cool Flex, & Trophy Boy
C-IN2 Profile Briefs, Sport Briefs, Street Jocks or the Personal Fit Factor Shower Brief
Calvin Klein Steel Collection, Body Collection, X Collections
John Sievers All Collections
N2N Bodywear Peformance X, Air, & Freedom Collections
Obviously For Men All Collections
My underwear collection is over 150 pairs deep, and while I have my favorite pouch, I like many more than just one. My favorite pouch is the Andrew Christian “Anatomically Correct Pouch” which is featured most prominently in the label’s “Almost Naked” line. The Anatomically Correct Pouch is formed by two seams that will allow all of your endowment to fall into place and hang naturally. To me, this is the best pouch for us well-hung guys, but obviously it is far from your only option.
Tip #2 – Expect but Accept “Sticker Shock”
All of the underwear best suited to the needs of men who are packing heat has one thing in common, they aren’t cheap. To create the best pouch for well-hung gentlemen, like the Anatomically Correct Pouch from Andrew Christian or brands that only feature this sort of pouch (John Sievers, Obviously For Men) you need human innovation as well as fabrics that are meant to stretch comfortably without stretching out, and those things are expensive.
You can expect to pay similar prices to the Calvin Kleins and Armanis of the world, not because of name brand recognition, but because of the use of Rayon and Modal fabrics. Briefs, Boxer Briefs and Trunks will run you anywhere from 16-30 depending on design and brand. More important than your expectation of seeing those prices is your acceptance that this is what you must pay to cloth your larger than average package on a daily basis.
But before we move on to the next big tip, let me give you two inside tips to get the best prices and value from your new, properly fitting undies:
1. Wait for sales. The best place to shop for men’s underwear is online. You can buy Calvin Klein Underwear at 25% off nearly year round online, and the biggest underwear websites (Freshpair, MensUnderwearStore) have routine sales on all their brands and clearance sales year-round.
2. Wash Separately, In Cold Water, and DO NOT DRY*.Unless you’re 12 and still can’t wipe properly, there should be no reason to wash your designer underwear in hot water. *Do not dry on anything higher than “medium” heat if you must dry at all. If you’ve got a normal 8-12 pair arsenal of Rayon/Modal underwear with the pouch made for men like us, know this: That fabric dries quickly when the underwear is laid out neatly, because the fabric is thin, constant wash-dry cycles shorten the lifespan of the fabric and the seams that attach it to the waistband. If you do this right, those $24 Obviously trunks will last you twice as long as the ill-fitting Hanes you wear now and thus you’ll have at worst spent about the same amount of money.
Tip #3 – Educate Yourself about Design, then Open Your Mind (Hint: I’ll help w/both)
Your education has been started with Tip #1. So, by now you unequivocally know that you shouldn’t be wearing any underwear that does not come specially designed in one of several ways to hold and support your large equipment comfortably. And of course the pouch is and always will remain the most important feature of any pair of underwear for men who are well-endowed. But a contoured or specially made pouch isn’t the only design element in men’s underwear that can be beneficial to those of us who require that extra room. It layman’s terms, not all pouches, are made with us in mind, are created equal. To get the best pouch for your boys, it may require you to open your mind about what underwear designs you need to try, I had to and did.
With very few exceptions (certain brands), if you’re well-endowed and searching for underwear that will give your boys the most room and do so in the most comfortable fashion, you need to be buying briefs, and once you’ve totally opened your mind, the skimpier they are, the more comfortable your package will be. Instead of wasting lines convincing you why you’ll appreciate the switch, I’d rather explain why briefs (and even skimpier options) are best for those of us well hung individuals.
Think about the appearance of the letter “U” both in lower and upper case, then think about what the pouch portion of a brief looks like. The larger the “u” or “U” shapes get, the larger the pouch becomes, and for well endowed men, we are best served by the biggest U possible. In underwear design this is achieved almost solely by the “cut” of the brief, chiefly the distance between the top of the leg opening and the top of the waistband. The larger the distance, the smaller the ‘u’ shape of the pouch, conversely, the smaller the distance, the larger the U. Here are two examples of this design concept from the same brand, 2xist: Example 1, Example 2. Now I could go on and on about this concept and how important it is for well-endowed men to remember when underwear shopping, but I won’t, I think you get it. I will only say that if you have accepted the concept, you may have your mind opened to trying jockstraps as something you can wear for a day’s length, and gasp, maybe even trying a thong! But because design concepts change a bit for jocks and thongs, I’ll devote a smaller article to those later.
Tip #4 – Lastly, Embrace Your “Gift” and Start Having a Sense of Humor about it.
You’ve made it! Congrats! So now that you know that A.) You don’t have to suffer through the rest of your life wearing underwear made for the 98%, and B.) you know enough to successfully explore your options, it’s time to embrace your “gift” and enjoy your new underwear. I am over three years removed from these discoveries, and throughout that time, I’ve learned to have a sense of humor about “my gift” if for no other reason than my underwear forced it upon me.
Most of the underwear that is either made for men with large packages or at least accommodates them, are going to end up showing your goods off. I remember when I got my first pair of Andrew Christian briefs in the mail and tried them on, and all I could do was laugh at my reflection in the mirror. And while I will contend to the death that at least I remain humble about the size of my package, as do most of us in the “well-endowed crowd” (pardon the silly rhyme), far too often, such ‘required humility’ is what is holding us back from wearing the underwear that is best suited to our needs.
So use this guide, and go get yourself some better fitting underwear. Your body will thank you!
NOTE: If you enjoyed this read more in our Endowed Series
This is the first pair of thongs I have tried in a while and, I must tell you, I was a little unsure about wearing it. My wife bought me a thong for our honeymoon many years ago and it had a basic string back. This pair had about an inch worth of material instead of a string. I was not sure how comfortable it would be having that much resting in the vertical smile. 
