How to Wear Boxer Briefs Properly

How to Wear Underwear for Men: Boxers, Briefs and More

Let’s kick this off by saying: this guide isn’t meant to be condescending in any way. We absolutely believe in your ability to slip on a pair of pants. You find the front pouch, put your left foot in the left hole, put your right foot in the right hole, and pull the pants up until they sit comfortably on your waist. Nice and simple… right?

Well, there’s a little more to it than that.

This guide is intended not only to ensure that you are pulling on your beloved pants in the correct manner (which, if you weren’t, now you know!), but to guarantee that you find the very best fitting pants and experience the greatest comfort possible.

That’s why it’s imperative that we go over the finer points of exactly how to wear your pants – of all shapes and sizes. After all, there’s little worse than an uncomfortable pair of pants. 

Is there a proper way of wearing underwear?

Now, we’ve already gone over how to pull your pants on. You find the front, put your legs in the holes, and pull the pants up to your waist. Done.

But let’s make some finer adjustments – pay attention, 007. 

First, let’s turn our attention to the pouch. Most modern pants (except loose boxer shorts) are designed to provide support for your package, to cradle it comfortably and keep everything in position. To stop it flopping about. 

To get the best fit, we’d recommend some adjustments. Get a hand in there and make sure everything is sitting in a comfortable position. After that, the pouch should snugly keep everything in. And make sure your balls aren’t packed too tightly – key for keeping up a high sperm count. 

Next, focus on the legs. You want to avoid material bunching, so pull down the rims of the leg holes and ensure a smooth fit to prevent chafing. 

How should underwear fit?

Underwear should sit against your skin on the legs and hold your package comfortably in the front. The waistband should sit at, or just below, your waistline where you normally wear your clothing – it’s different for everyone, so find the most comfortable spot.

But – and here’s the crucial part – different types of underwear should fit in slightly different ways. So, let’s get into it.


How to wear different types of underwear

Different underwear types have different cuts, lengths, materials, fits… it’s all quite complex when you get into the finer details. 

To save some time, the waistband of any pair of pants you slip on should sit (unsurprisingly) at, or just below, your waistline - where you normally wear your clothing. It’s different for everyone, so we’ll leave it to you to find the most comfortable spot. 

Now, let’s break down how to slip on the major types.


Boxers are the easiest in terms of fit. They’re designed to be loose fitting, so it’s as simple as sliding your legs into the holes and pulling them up with the fly or opening at the front. There’s no adjustment needed. No shimmying of the balls, no pulling of the leg holes. Everything should hang perfectly and loosely in place. 

Until you put clothes over the top of them.

In that case, simply make sure the excess leg material isn’t bunching up underneath the clothing. Then you’re good to go! 

Boxers are also perfect for wearing on their own as loungewear or sleepwear.


Briefs allow you to skip a step in the adjustment process. Once you’ve pulled them on, make sure nothing is feeling too pinchy or tight – and make sure your package is sitting comfortably – you’re all done, sir. That’s because briefs are a very short style and do not have any material to cover your legs – so there’s no need to worry.

Boxer briefs

Boxer briefs are like… long briefs. They have material covering your legs about ⅔ the way down your thigh. Similarly, they shouldn’t feel restrictive or tight. They are intended to complement your body shape with an elastic fit that provides equal measures of support and comfort. They should sit against your skin on the legs and hold your package comfortably in the front. 

Now, with these, in addition to adjusting your front pouch, you’ll want to make sure that the material is extended comfortably down your legs and not bunching up when you pop your clothes over the top. 


Trunks are, essentially, shorter versions of boxer briefs. The material on the leg only reaches about ⅓ to ½ the way down your thigh – so there’s less material to worry about when making your final adjustments. Make sure you don’t skip the leg adjustment phase though.


Thongs are unique in the pants world. You’ll want a pouch adjustment, yes, but while you don’t have to worry about a leg adjustment, you will need to do a string adjustment at the rear. 

Thongs and G-strings have a thin strap of material that runs from the waistband and through your buttocks to the front pouch. You’ll want to make sure that this strap is sitting nice and comfortably between your cheeks to prevent chafing and boost your comfort. This step is crucial for achieving a great fit with a thong – don’t neglect that strap. 

How tight should underwear be?

Underwear should not feel restrictive or tight – no matter what type you go for. While boxer shorts are designed to be loose, you still want the waistband to feel comfortable against your skin without any pinching or chafing. 

All other types on our list are designed to sit closer to your skin. They are intended to complement your body shape with an elastic fit that provides equal measures of support and comfort. Again, there should be no pinching or chafing at all. Not in the pouch. Not at the leg openings. If you’re experiencing any of these symptoms, then, unfortunately, your underwear will be too small for you – it’s time to size up. 

How do I know if my underwear is too small?

You’ll know your pants are too small if:

  • You find it difficult to easily get your legs in the leg holes and comfortably pull them up to the correct position. 

  • You find that instead of sitting comfortably against your skin, they’re squeezing you in any area. They should never do this. 

  • The waistband is digging into your skin. 

  • Your package is being uncomfortably crushed and/or completely restricted by the fabric. 

  • You find it difficult to get a full range of motion with your legs. 

  • The strap on the thong is really digging in.

If you experience any of these uncomfortable side effects, then it is a very good sign to seek out a new, better-fitting pair of pants on the double. 

Bonus tips on how to properly wear your underwear

Want some more detail on the best ways to achieve maximum comfort from your brand new pair of pants? Look no further than this list:

1. Find your most comfortable waistband spot

The perfect waistband spot differs from man to man, but typically it’ll sit on your hips and follow the line on which you normally wear your other items of lower-body clothing – hopefully you’ll know just where your perfect spot is.

Remember that no pair of pants you wear should have a waistband that digs into your skin. It should be resting against it comfortably, so that you can feel the elastic working. If it’s digging in, your pants are too small, sir. 

If you want to get the best waistband fit, measure your waist with a string rather than guessing your size. It’s a great idea to be a bit more precise with this as it will ensure that you get a close, comfortable fit that doesn’t dig into your skin. 

2. Ensure that the fabric is cradling, not confining

Every major type of pants except those loose boxer shorts should follow the contours of your body and not dig into your skin or restrict it in any way. They should provide you with a sense of comfort and security, not confinement and restriction. 

This is especially true of the front pouch. You want everything in there to breathe and feel supported. Not be mercilessly crushed 

3. Jimmy your junk

On the theme of private parts not being crushed, you want to stick a hand in there when you put your pants on in the morning and give everything a jimmy around. This will ensure that everything sits and remains in the position that feels most comfortable to you. 

Remember, they want to be supported and cradled in comfort. They don’t want to be crushed and abused. You want to give them a little room to breathe and ensure that everything is sitting comfortably and not at uncomfortable angles or flopping around all over the show. Let’s boost that sperm count while we’re at it, eh?

4. Smooth out the leg creases 

Finally, on everything except briefs and thongs, smooth out those leg creases and bunches. This will prevent chafing against the clothes you put on over the top of your boxers, trunks and boxer briefs. It’ll also stop any chafing from the pants themselves.

5. What if you’re between sizes?

Fear not! If you’re between sizes in any pair of pants, we would recommend the following:

If you have larger than average thighs and you’re looking at trunks or boxer briefs, it is a good idea to choose the size up. This will make sure that you get a more comfortable and less restrictive fit. If you have average to small thighs, then go for the lower size. 

Pay attention to the size of your member as well – relevant for thongs and briefs too. For those among you who are well-endowed, you may want to choose the size up to prevent any restriction or discomfort in the pouch.

Choosing the right underwear for you

So, ensuring you have the best fitting pants and that you are wearing them correctly is more complex than it first appears, yes?

Above all else, you want to avoid any tightness and pinching from any pair of pants. They should be comfortable, supportive, and a pleasure to wear. Boxer shorts should be loose and flowing, but without too much excess material or a tight waistband.

If you need more info on how to make sure that you get the best-sized pants for your body, then check out our comprehensive size guide (complete with chart). Or, if you want to take a deep dive into each type of underwear in more detail, then take a gander at our complete underwear style guide to find your next favourite pair.

Seen something (or things) you like? Get on over to our site and shop our extensive range of men’s pants. We have something for everyone.

Now, go forth, safe in the knowledge that you know how to properly wear all the major types of men’s underwear correctly. You little beauty.