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How any pairs of skivies should a man own?

Seven.

I have the days of the week embroidered.

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musicman1951

three-tu-tu, three-tu-tu
Two. You should get four days from each pair:

Day one - normal
Day two - backward
Day three - insideout
Day four - insideout and backward

After four days they really need to be washed.
 
I think this all depends on one's lifestyle. My rule of thumb is, take the amount of days you typically take off for vacation and add 2.

If you aren't one to take vacation, I think 8 or 9 is all one really needs.
 
42?

Two. You should get four days from each pair:
Day one - normal
Day two - backward
Day three - insideout
Day four - insideout and backward
After four days they really need to be washed.
Big Hero 6?
I was wondering who would bring that one up. My son is nearly potty trained now and when he first started wearing real underwear he said that every time we put a fresh pair on him.
"I haven't done laundry in six months. One pair last me four days-- I go front, I go back, I go inside out, then, I go front and back." - Fred

Now that the movie and book references are out of the way, I would say 14. Enough for a full week, plus extras on exercise days, plus a couple for margin to get laundry done.
 
The original question is how many should a man own. I figure that a person can only answer that for himself. So any number from zero on up can be correct, depending on the individual.
 
Maybe eight pair of briefs (two of which have a weird fly and only get used for sports), a few pair of boxers used mostly for sleeping and a couple pair of "boxer briefs" that were in hindsight a huge mistake - bunchy and way too hot plus a couple pair of long johns for winter sports. If I could do it all over, I would just get three pair of good travel briefs (such as ex-officio) that you can buy from any number of purveyors. Breathable, lightweight, quick drying (sink wash at night and dry well before morning), pack well and possess an antimicrobial lining to keep your big boy pants fresher for longer.
 
I don't like doing laundry. Underwear and button-up shirts are the major limiting factors, so I keep their numbers roughly even.

I never thought to count, but I know I can go at least three weeks before I have to wash and iron a shirt, so I must have... around 20?

As long as they can all fit in one drawer at the same time, I don't think you have anything to worry about.
 
Zipper entanglement prevention.

No free hand on a windy day to hold the kilt down?
 
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