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.

To Bulge or Not To Bulge

All Men Have a Bulge

Let’s get one thing out in the open right off the bat – men have penises, dicks, cocks, junk, a package, a johnson, or whatever you want to call it (if you can’t decide then check out this list of 167 slang words for penis to help you decide –  It will apparently come a shock to some people, but there you have it – men have dicks, I have one, if you’re a man reading this you have one, if you’re a woman reading, this every man you have ever met or ever will meet has a dick, and sometimes you’ll be able to see it – even if they are dressed.  Much like women have breasts and sometimes, even if they are dressed, we can still see them, but this blog is about men and their stuff so we’ll put the breasts away and move on.  This post is about our bulges, or VPL – visible penis lines, and what if anything to do with them.  To misquote a famous writer we will discuss whether to bulge or not to bulge.

For the most part, your package is almost always visible at some point during the day and most guys , myself included, don’t really think about it or care.  The problem that arises (no pun intended) is when your bulge becomes very pronounced in circumstance or places where it may not be that appropriate, like at the office, at a children’s sporting event or birthday party, or whenever, you get the idea.  It happens all the time, look around sometime when walking around or watching TV they are everywhere:

At work:

Suit Bulge

Suit Bulge

VPL at work

VPL at work

Playing Sports:



Football palyer

Football player

On the street:

Business Mna

Business Man



Average Joe

Average Joe

What is wrong with bulges?  In a word, nothing.  In my opinion, if you don’t want to see a mans bulge, then don’t look at his crotch.  The reality is, that there are plenty of people who choose to be offended by almost everything around them – yes I said choose.  To be offended by my or anyone elses bulge is 100% your choice and if you have chosen to be offended then get over it and go on with your life because that is a stupid choice to make.  That being said, there are times when it is inappropriate to show off your junk and there are things you can do to lessen it, mainly wear underwear that does not have a pouch to lift up your dick and display it to the world but instead a more modest style that style provides comfort without the lift.  Going commando at your 7-year-old nieces’ birthday party is also probably not a good idea, especially if you are wearing sweatpants:

Sweatpants VPL

Sweatpants VPL

Sweatpants bulge

Sweatpants bulge

Use your common sense and save the show for more appropriate locations.

I am not, by any means, saying hide your dick all the time everywhere you go.  Just be smarter about it, instead of freeballing at the office so Pam in accounting can make a complaint to HR about your cock always swinging into the room a few seconds before the rest of you – wear underwear to keep it under control.  If you like the freedom of no underwear but require the control for the sake of office politics then try g-strings or jockstraps.  They give support in the front without restricting movement and they are open in the back so you get the feeling of wearing nothing (check out for a few suggestions).

If you want to show the world what you have to offer and don’t give a damn who sees your bulging package then go ahead and put yourself on display and let the chips fall where they may.  Some guys like the attention of coworkers, people on the street and anyone else taking quick glances or long stares at their crotch and that’s fine you’re fine with it.

There is also a group of men that have another issue – they are huge, hung like mules – and the issue isn’t so much with showing off their dick, but instead they actually have trouble concealing their bulge regardless of what Pam in accounting wants.  That can be a problem for some guys (I said some – I am aware some don’t have a problem).  Some of the problems can be – in the workplace drawing unwanted attention, people looking at your cock instead of your face, unwanted comments about your appearance (is any of this sounding familiar ladies?  Yes it happens to guys too and it is just as inappropriate);  at the gym ‘falling out’ of your shorts (yes it happens), getting unwanted attention in the changeroom and showers, excessive flopping around when doing cardio and so on;  on the street people making rude or unwanted remarks, actually getting chastised by some exceptionally prudish passers-by;  in day-to-day life depending on the size your shaft can splash down into the toilet when you sit down, or trying to hide an unexpected hard-on (which can be difficult regardless of your size) can be next to impossible.  Most of these issues can usually be fixed with properly fit underwear which is a topic I will discuss in a future post about how to properly fit underwear for your body size and dick size.

Essentially the basic thing to take away from this that is as a man you have a dick, be proud of it but don’t stick in everyone’s face.  Dress to be comfortable and feel good first, look good second and please others last.  Don’t hide your package and don’t be ashamed of it.  Just have common sense, I know this can be difficult for some people, but try real hard not to make your cock the focus of a childs’ bar mitzvah or birthday party and use a laser pointer to draw attention to the pie chart during the business meeting not the shadow of your giant bulge.  There is a time and place for everything.

Thanks for visiting – feel free to add your comments and offer your opinions