Briefly

Because The Dapper Tightwad does not have to see your skivvies, there is no advice or rule to offer on this subject, save this:

I do NOT have to see your skivvies.

Seriously. No one needs to see that you are wearing boxers. Or briefs. Or some preposterous plum-smuggling, Dirk-Digglerizing donglonger doodad. I am not hating, I just really do not need to see that anymore than I need to see your granny in her Spanx or your whale-tail waving from your low-low-low-rise horizon.

You no doubt have your own preferences, which I will respect automatically, what with the you-not-showing/me-not-seeing thing above, trusting instead that you have developed your preferences over the years with the wisdom of accumulated experience. What kinds of experience? Funny you should ask. Perhaps you have encountered one or more of the following phenomena:

1. Boxers under snug blue jeans on a humid day. Result: the downtown taquito.
2. Failed elastic on a long flight. Result: the slideways.
3. Insufficiently supportive briefs in yoga class. Result: unhappy baby.
4. Going commando under microfiber slacks. Result: sheer entertainment.
5. Difficulty conceiving

In any case above, you know what to do. If you want to have some fun and derring-do with your underpants, I applaud you, but no one is really looking. On the other hand, if you endeavor to feel chaste and secure in your choice of conservative briefs, keep in mind that there are settings where the tighty-whitey is the height of fabulous fashion. Underwear is nothing if not treacherous.

Finally, it should be noted that The Dapper Tightwad, though an inveterate thrifter, buys only new-in-the-package* package packaging. Though I will not turn up my nose at a dead man's shoes in the Goodwill, I have never even looked at the price tag on a pair of underwear in any thrift store. It's an ick thing.

But hey, no one's looking.

Frugally yours,

TDT

* A loyal reader suggests the modifier "untainted."