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How to Wear Boxer Briefs Properly

How to Wear Boxer Briefs Properly

We should probably start by saying that this guide isn’t meant to be condescending in any way: we’re pretty confident that you know how to put on a pair of boxer briefs correctly. 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. 


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

Boxer briefs are a hybrid of both boxers and briefs, combining the fabric coverage on your legs of a boxer short, with the supportive elasticity and cradling comfort of a pair of briefs. They’re stylish, they’re comfortable, and they’re the most popular style of men’s underwear on the market today. 

That’s why it’s imperative that we go over the finer points of exactly how to wear boxer briefs to ensure they give you the best fit and most comfortable experience possible. After all, there’s little worse than an uncomfortable pair of pants. 

Is there a proper way of wearing boxer briefs?

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

But it is in the finer adjustments where a good pair of boxer briefs can be made astoundingly comfortable or unnecessarily painful to wear. So, pay attention, 007. 

Once you’ve pulled the boxer briefs to your waist, your next area of attention should be the front pouch. Boxer briefs are designed to provide support for your package, cradle it comfortably, and keep everything in position to stop it flopping around all over the place. 

To achieve this, we advise getting a hand in there and jimmying everything about a bit. Make sure everything is hanging comfortably in a position that you like, because once it’s there, it’s the job of a boxer brief to keep it there. Be careful to make sure that the balls are also cradled by the material and not crushed or suffocated by it - a very important point when it comes to keeping up a high sperm count too. 

See, there’s a lot to think about with properly fitting pants.

Next, turn your attention to the legs. You want to avoid material bunching on the legs, so make sure to pull down the rims of the leg holes and ensure a smooth fit against your skin. This will prevent chafing against the clothes you wear on top of your pants and is an important step not to be missed. 

How should boxer briefs fit?

Boxer briefs should not 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. 

The waistband 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. 

How do I know if my boxer briefs are too small?

You’ll know if your boxer briefs 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, the boxer briefs are 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. 

If you experience any of these uncomfortable side effects, then it is a very good sign that boxer briefs you are wearing are too tight for you. If this is the case, you should seek out a new, better fitting pair on the double. 

Tips on how to properly wear boxer briefs

  1. Find your most comfortable waistband spot.
  2. Ensure that the fabric is cradling, not confining. 
  3. Jimmy your junk. 
  4. Smooth out the leg creases.
  5. What if you’re between sizes?

1. Find your most comfortable waistband spot

As we’ve said, this differs from person to person, but typically sits on your hips and follows the line on which you normally wear your other items of lower body clothing. 

Remember to bear in mind that the waistband on boxer briefs should NOT be digging into your skin at all. It should be resting against it comfortably, so that you can feel the elastic working, but not digging in. 

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. Remember, you want it to sit on your skin and stay in place, not uncomfortably dig in. 

2. Ensure that the fabric is cradling, not confining

Boxer briefs should follow the contours of your body and not be digging into your skin or restricting 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 enough room for everything in there to breathe and feel supported. What you don’t want is for it to feel crushed. 

3. Jimmy your junk

And, on the theme of your 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. 

4. Smooth out the leg creases 

Finally, smooth out those leg creases and bunches. This will prevent chafing against both the clothes you put on over the top of your boxer briefs, but also against the boxer briefs themselves as you walk.

5. What if you’re between sizes?

Never fret!

If you’re between sizes, we would recommend the following:

If you have larger than average thighs, it is a good idea to go for 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. 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 boxer briefs for you

So, ensuring you have the best fit of boxer briefs 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 your boxer briefs. Think of them as a second skin over your body. They should be comfortable, supportive, and a pleasure to wear.

If you need more info on how to make sure that you get the right size of boxer brief for your body, then check out our comprehensive size guide (complete with chart).

If you’re thinking that perhaps boxer briefs may not be for you, then take a good long look at our complete underwear style guide and find the magic pair.

Now that you’re fully prepared to step into an amazing pair of boxer briefs, it’s a good idea to explore our Pants & Socks range.

For anything else, get in touch with our team, who are always more than happy to help with anything ‘pants’.

Now, run free and choose the very best boxer briefs for you and your body!

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