The quest to answer this question has existed since there became a choice.  And here’s the real reason for the question:  Bulges and their perceived prominence.  I mentioned yesterday that my biggest issue is with guys tucking in the shirt in the front and not the back because it basically amounts to a codpiece the way the pants look (they are almost always too big in the waist).  

Now, my father and his father would swear that briefs were the way to go.  They maintain the bulge, allow for some support of the goodies and they are pretty comfortable.  Many of my contemporaries would say that boxers are the way to go.  They allow some freedom and they – well, I’m not sure.  See, the only reason I could see to wear boxers are to keep the last 1 drop of pee from coming through the pant.  Oh, and I guess they would keep the penis from rubbing against rougher material (denim).  Then there are those who wear boxer briefs, which are exactly what they sound like (and if you buy them in too large a size, you basically bought boxers).  

But I should point out that if you pop a tent in your boxers and you don’t have a way to maneuver the penis to be discreet, it’s gonna show. A LOT.  Same with briefs.  But with the briefs, chances are your penis is already in a discreet position that will allow you to maintain dignity should you get a boredom boner or something.

From a sartorial standpoint, it’s preference.  Now, you shouldn’t be able to see them through your pants. I tend to think that’s the only thing that should be a guideline.  With linen you are should wear underwear.  If it’s really lightweight linen, you can go with a nude colored underwear.  I’ve read some people saying that it’s better to go with white underwear with white lightweight linen.  I don’t agree.  Everyone will see it and while everyone knows you wear underwear (or at the very least assumes it), you don’t want to confirm it.  Better to save a little mystery for your co-workers.

Otherwise, whatever color/cut/style/size you choose will work wonderfully.  Oh – except for thongs – be careful here, gents.  The men’s thong is a nice piece of underwear, but do make sure that the thong doesn’t come out the back.  No one wants to see a “whale-tail”, much less on a man.

Do you really want to see this, ever? (unless you like this, in which case, go to a gay bar on underwear night!)

I rest my case.

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This recently came up at my job about and it never occurred to me that this needed to be addressed after the fifth grade, but here we are:  Tucking in a shirt and when to do it.

Some people will have you believe that all shirts are meant to be tucked in.  Certainly there are those who just feel better having the security of a shirt cinched by the belt.  And as with most spectrums, there’s the other end of it; the guys who never tuck in a shirt.  So, here’s my personal feelings as to tucking and untucking.

Untucked:  T-shirts, Polo Shirts, Rugby Shirts.  That is all.  These have a straight hem and are meant to be worn out.  However, you can tuck Polo/Rugby shirts in.  That is because they have a dressy/buttoned collar and lend themselves to dressing up a pair of pants. 

Tucked: Any shirt with tails.  ALWAYS TUCKED IN; NO EXCEPTIONS.  Now.  I will say that I have a shirt that I usually wear untucked.  This is because it is too small to actually stay tucked in (there are products that combat this effectively – one is sort of a rubber belt that goes between the underwear and the pant).  The solution?  I got rid of it (which was a shame because it fit wonderfully otherwise and you wouldn’t believe it, but it never wrinkled).

Pants to tuck?  Anything you might think is dressy?  Should have a belt and be tucked in.  And yes, folks, there are dressy belts and casual belts.  I know, I know, it’s hard to believe – but seriously.  Wear a good belt with good pants and wear the LED-scrolling belt that says “CHAD RAWKS” with your Diesel jeans.  On second thought – don’t ruin Diesel’s good name with that. 

Oh – one thing to avoid: STOP WITH THE HALF-TUCK.  The tuck in the front to show off the buckle and then leaving the rest out?  Seriously, it’s the equivalent to a codpiece.  And what straight male wants to walk around with their crotch showing all day.  Most of the ones I know might as well be Ken dolls with how little they like to show their crotch.