Have you ever bought a pair of underwear that looked great on the model but not nearly as good when you’re trying them on at home? Too tight in some places, too loose in others, or the wrong size altogether… It’s frustrating especially when you’ve spent $20 – $30 or more on a single pair. I know this experience well and so over the next several weeks I’m going to be posting tips based on my own experiences on how to find a pair that will fit you well.

This week’s tip starts with the very basics (for first time buyers); sizing. You can’t expect to order a pair of underwear that fits if you’re not familiar with your own body! So it’s time to spend a few minutes checking yourself out.

TIP #1 – Know Your Body

Measure Your Waist:  The only measurement you’re going to need when ordering underwear is your waist size. These days most designers will measure the waist as the distance around the top of your hip, roughly 1-2” below your belly button. Remember to pull the measuring tape tight enough so that it’s not hanging down at the back, but not so tight that it’s digging into you. Don’t rely on the waist measurements of the jeans you wear as jean sizing can often be an inch or two off. I used to wear size 32” jeans and so by default I’d often buy size medium underwear, which were always on the loose side. One day I decided to take the time to actually measure my waist and found that I was actually 30.5”!

Check Sizing Charts: Next check out the sizing chart/guide on the website you’re ordering from (usually found at the bottom of the main page or under their FAQ or Help pages). In the description they’ll give you the appropriate size for each waist measurement range along with other fit considerations. If you’re looking at a retailer website (one that carries multiple brands, such as International Jock or Fresh Pair) you might want to refer back to the specific designer’s website for the item you want to buy as it’ll have more accurate sizing info. I have come across products that do fit smaller/larger than what’s posted in the size chart but it’s not common. An example of this is ‘Go Softwear’ products which tend to fit small, although the brand has now updated its FAQ page to state their products have a ‘European fit’ (they fit tighter than usual). If you can’t find a brand’s size chart try doing a google search (eg/ ‘Gregg Homme Sizing’) as sometimes the sizing chart is hidden somewhere on their website.

Remember Your Butt & Package: When ordering you should also consider the size of your butt and package as these can affect how well a pair of underwear fits. Try on a few pairs you have in your drawer and see how well you fill them out in the front and back. If they look baggy, but the size ‘should’ be right, then you might want to consider a smaller size. If you have a large package and butt and underwear generally fits tight then it might be worth trying a size larger than what your waist measurement says you should get. If you’re in between two sizes your package and butt will also help you determine if you should go larger or smaller – or you can go with how you like your underwear to fit (snug vs. relaxed). At 30.5” I’m at about what’s typically considered a size small. Even though I can get away with a size medium I’ll usually go with a small as I like the tighter fit. I’ve also found that a lot of underwear tends to stretch out some with wear, so buying small means they’ll only fit better with time.

If you’re considering contoured/pouch underwear know that they’re typically designed to fit the ‘slightly above average’ guy though some fit larger (such as Gregg Homme) and some fit smaller (such as Good Devil). Since there’s no specific measuring system for pouch underwear use the suggestions I’ve given above. I’ll go into more detail on finding proper fitting pouch underwear in one of my future tips. Pouch size will often increase with larger sizes.

Learn from Experience: If you’re ordering a pair from a designer you’ve ordered from before, see how the previous pair you’ve bought fits. Designers generally maintain consistent sizing across styles, so the previous pair should give you a good idea of what to expect. For example, I’ve found that Calvin Klein gives you more room in the back than other designers such as Diesel. So whereas with Diesel I might sometimes be tempted to go with a Medium for a slightly more relaxed fit, with CKs I’ll always get size Small.

Even after all these sizing considerations designers create their products based on different body types so there is no guarantee that your next pair of underwear will fit as well as you had hoped. Catch my next posts to learn more tips on how to find a designer and style that best fits you.


Tim is the founder and editor of Underwear News Briefs. He has been an avid underwear fan since the age of 14! He founded UNB in 2008 and has continued to broaden his underwear love over the years

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