There have been many demographic diaries on Daily Kos, so just add this to the list. I'll offer my interpretation of what your choice or undergarment means about your politics. This will be a completely subjective perception, feel free to offer your own.
This topic really came into the mainstream during the Clinton Administration when it was asked of Bill Clinton. Some celebrities had been asked this before but it had not been asked of a national politician. From this perspective I'll offer my take on what this means politically.
BRIEFS
As little boys most of our mothers put us in briefs, it a bit of an extension of the diapers we had been wearing. It's accepted at this level for all males to wear briefs and it will usually have no indication as to your future political leanings. However, our transition to our preference has been a moving target. But by your mid-twenties to early thirties you should be settled in. So if you're in that transitional period, you still have some time to commit to something else.
From my perspective, those still wearing briefs into their thirties and beyond are expressing strong conservative leanings. This can be reflected in their personal life or their public political life or both. There is a reason they are referred to as "tighty whities", they tighten up more than your package, your brain for instance. You see, for guys these are often tied together ( your brain and your package). You may also be "controlling" of many other issues in your life.
BOXERS
Today you'll often find more teenagers wearing boxers (or boxer/briefs, which I'll cover below) today than you did when I was a teenager. When I was a teenager you could have 85 guys on a football squad an not see one pair of boxers. I think you'll find those numbers have dramatically changed. I'll not get into the teen demographics, there are dozens of reason for the change in those numbers.
However, as you mature into adulthood and you political perspective starts shaping other parts of your life it may well be expressed in your choice of under garment. Boxers are an expression of your more open attitude on life. Your personal beliefs may be conservative but you don't impose your views on others. Or you may be expressing your own openness or progressive views if you will. You are less likely to be judgmental of others.
COMMANDO
Now this lack of wearing an under garment has several interpretations. In days gone by this was seen as a lack of conviction to a belief in anarchism. Today, there is still no definitive interpretation. Teenagers do it because they think it's sexy (you won't find the baggy britches wearers going commando). Conservatives may do it as they attempt to show their belief that it makes them more macho than they are. Progressives may do it as an expression of a step beyond openness to one of complete freedom.
Regardless of why you're going commando, it's doubtful you do it all the time. You have a fallback garment.
BOXER/BRIEFS
These are transitional garments. Teenagers wear them as well as twenty somethings. If you're wearing these beyond 30, odds are you're still confused or your wife bought them for you to get you out of those damned tighty whities.
I'll post a poll below so you can express your choice. For the ladies, check what your husband/SO/partner wears. Or if you are currently single, your preference in a prospective partner.
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MKinTN posted a diary to help everyone achieve greater success called How to Succeed at Mojo Friday Without Really Trying.
For those of you new to MF (Mojo Friday) we have our own lingo about a few things. Thank's to MF'er Jez (the link will explain) go to this diary for a little more fun and explanation. Official Mojo Friday Snecktionary.