Tips For Picking Great Underwear

Proper Fit + Comfort = Great Underwear for Men

Trust me – there is more to picking underwear than just looking for the cheapest multipak of bargain tighty whities on the shelf.  If you want to find the most comfortable underwear that you can then I have a few tips for picking great underwear.   Most men spend a significant portion of their waking hours in underwear of some sort, either briefs, boxers, trunks, jockstraps or g-strings.

The first step, obviously, is to decide what style you want (don’t limit yourself to one and only one style or brand – guys are terrible for this.  We find something we like and we hang on to it like grim death).  There are a few examples above, I will briefly touch on their differences:

  • Briefs – they get their name from the fact that they are brief – they provide full coverage in the front and back and are the most common
  • Boxers – when I refer to boxers I will be talking about the form-fitting still pictured above, not the loose and baggy things that almost no one wears anymore.  These provide full coverage in the front and back but also go farther down the thighs
  • Trunks – basically a square-cut boxer – usually with a lower waist and higher leg on the thigh
  • Jockstraps – a pouch in the front to hold your cock and open in the back with leg straps going from the side waistband under each butt cheek and connecting to the bottom of the pouch between your legs
  • G-string – a pouch in the front connected at the waist to a string waistband with another string going from the back of the waistband between your ass cheeks and connecting to the bottom of the pouch between your legs

Once you decide on a style then there are 4 different parts of your body that you should take into consideration before you even start actually looking for some new undies:

  1. Your waist – or if you are looking for low-rise then wherever the waistband of the undies will sit.
  2. Your legs, particularly upper thigh
  3. The size of your dick
  4. Your ass

Where is your waist

When Measuring the waistline use a measuring tape and wrap it around your waist and firmly (but not too tight) along where the elastic waistband would be, roughly 1/2 to 2/3 of the way down the line from your belly button to the base of your shaft (pictured below)



Keep in mind this is a personal preference thing as well, some guys like it a little higher, some a little lower – that is up to you but the measurement taken here will usually translate well for an inch or two in either direction.  The number you get will be your waist size.  Most mens underwear is sized according to small, medium, large and x-large (and so on) and it is important to look at what these four sizes translate to in number form – they differ between manufacturers.  A medium from brand X could fit a waist size 30 – 33 whereas brand Z has it fitting 32 – 35 – check it out before buying.  You don’t want to end up spending $20 on a pair of underwear that leaves a semi-permanent mark on you for a few hours after taking them off, especially since underwear can NOT be returned at any reputable website or store.

What about your thighs

Measuring your legs is generally more important if you have thick legs due to working out a lot or if you are overweight.  Underwear can become very uncomfortable very quickly if it feels like you have a tight elastic band wrapped around your thigh.  Depending on the type of underwear you are getting, where you measure may change (see the image below).

thigh line

Thigh Line

The pink line (top) for briefs, the blue line (middle) for trunks, and the green line (bottom) for boxers (the length of boxers may vary by design or brand).  It is safe to say that for most people the width of the leg holes will coincide nicely with the waistline, this really is only a potential problem for men with thick thighs.  you most likely already know if this is an issue for you and if it is a way around uncomfortably tight underwear is to get boxers or long boxers since they come down further on your thighs.  If you have a problem with the legs riding up then you may want to consider a brand with a looser design around the leg holes.

Your Ass

This really only matters if you have large butt – sometimes called a bubble butt.  Average butt sized people can skip to the next section.

The only issue (if you want to call it that) that generally appears here is the line across your ass cheeks that appears when you either try to force a nice big ass into undies that are too small or too tight usually caused with briefs.  In extreme cases it can look like you have four ass cheeks but if you don’t care then I don’t either, if you do care then just don’t wear briefs, something with a longer leg,r a jockstrap or g-string and the quadra-ass will disappear.

Your Dick

Now the last big floppy thing to deal with.  If you are an average sized guy, I am referring to your cock size, then simply go with the small, medium, large and so on sizing mentioned earlier.  However, if you are of the above average cock sized men out there then you may want to make some extra considerations.  Cramming a huge dick into small underwear may look good when sexting or strutting around a porn set where they will be peeled off fairly soon, but in the real world it can be uncomfortable to painful after being coiled up in there for a few hours or longer.  Also if you end up just stuffing down along your leg then excessive sweating and itching can be another issue.


A lot of guys with extra-large dicks will just opt to freeball or go commando whenever possible but that isn’t always appropriate (see my last post about VPL).  The easiest way to provide comfort and support is to get a tighter fitting underwear that has a loose pouch sewn onto the front and get a size larger than your waist size would dictate.  What I mean is if you normally wear a medium then consider getting a large.  The larger size will provide a bit more room, and the loose pouch will provide more room and still give some support (an earlier post about pouches in mens underwear).   Search around for brands, and pay attention to the type of pouch.  This can make a real difference for your comfort.

Well there you have it, a few things to take into consideration when getting some new underwear in order to get the most comfortable kind you can.  If you have any other tips, email me – or if you think I’m full of shit email me that too.

Thanks, and come again,


Thanks to Blue Square Clothing for sponsoring this post – use the code – BLOGME25 – and you’ll get 25% off underwear until June 30, 2015.