A Men’s Guide To Choosing The Right Underwear Size

Part 1: What Size Underwear Am I?

I dunno. Large? I can’t see you. What size men’s underwear do you have on right now? Is it comfortable? Stick with that. Is it too tight? Try a size up. When you stood up to check, did your underwear loosely fall around your ankles? Try a size down.

Of course, if you want a more scientific method to find the most accurate fit possible, we’re here to help. We’ve gathered the world’s leading undergarment size-ologists and locked them in a room with the mission of creating the most thorough, easily digestible, and revolutionary underwear sizing process known to man. Unfortunately, we did that on a Thursday and then had a long weekend and came back on Tuesday and they had all died because we forgot to leave them water. Fortunately they had all signed waivers releasing us of any liability in the result of their untimely deaths. Talk about a close call! 

Point is, you don’t need a scientist to tell you how to choose a pair of underwear that fits. And today I’m here – with plenty of water nearby – to help walk you through the process.

Part 2: How To Choose Male Underwear Size

There are so many sizes of men’s underwear out there. But these days you practically need a degree in crypto-symbology to understand how underwear sizes for men work. You try to buy underwear online and the website confronts you with this coded nonsense:

mens underwear size guide

I’m sorry, is this a size guide or an algebra problem? What the heck do all those numbers and letters mean? Is that the Roman Numeral for 10, a multiplication sign, or a small treasure map?

Are we simply to assume that S means Small, M means Medium, L means Large, XL means Extra Large, and so on? Sure, that system makes perfect sense, but look around: When was the last time anything in this world made sense? Maybe S means Spacious, M means Massive, and L means it only fits people named Larry.

And just because you’re a Medium in one brand of underwear doesn’t mean you’ll be a Medium in our underwear. By the way, why are you wasting your time wearing other brands of underwear? 

Point is, we simply need more information to make an informed decision. Thankfully, finding your correct underwear size only requires a couple tools, some complicated charts, and a few hours of your time.

Part 3: Your Hips Don’t Lie: Using An Underwear Size Guide

Grab a tape measure (or tape measurer) and drop your pants. It’s time to figure out how big your waist and hips are. And if there’s time you can measure your penis too, but let’s try to stay focused. Here’s an illustration to help you along:

mens underwear measuring guide

  1. Measure your waist. This is the part of the body that your dad’s pants come up to. Pretty much right in line with your belly button. If you’re measuring where your grandpa’s pants come up to, you’ve gone too high.
  2. Measure your hips. This is the widest part of your butt region. Close your eyes and sensually rub your hands down your sides while imagining you’re a sexy lady. When you get to the sumptuous curves of her hourglass figure, stop and open your eyes. Those are your hips!

Then take those measurements again and this time remember to write them down so you don’t immediately forget. Hey, you’re doing great. We’re halfway there.

Wait! Did you measure yourself using inches or centimeters? If you used inches, proceed to the next step. If you used centimeters, slap yourself in the face, say the Pledge of Allegiance three times, and start over.

Now head over to our men’s underwear size chart to see how you measure up. Actually, you know what? I’ll just paste the underwear size chart right here. That’ll save you some time.

mens underwear size chart

A great way to double check that you used the boxer brief size chart correctly is to check out our men's underwear, decide on a fun print, buy a pair in every available size, and see which one fits best. Because if you’re like me, when you measured your waist earlier you totally sucked in your gut so you’d get a smaller size and feel better about yourself. But trust me, that good feeling goes away pretty quick when your underwear is too tight and cuts off circulation to your dick. I thought my penis had fallen off! Luckily – hold on, lemme check again just to be safe – it’s still there. And it’s more comfortable than ever now that I’m wearing the right size underwear. 

If the pair you’re trying on feels too tight on your waist, legs, or dangly bits, then switch to a size up. If the pair you’re trying on feels too loose on your waist, legs, or dangly bits, then switch to a size down. It may take a few tries, but once you find the Goldicocks pair that fits just right, you’ll enjoy comfortable underwear until the bears come home and eat you.

And Shinesty makes finding your perfect fit risk-free with free returns and a full money back guarantee. Trust me, getting you in the most comfortable underwear possible is as important to us as it is to you.

Stay Weird & Remember Those Hips Don't Lie