Answers to that question could vary depending on one's imbibing habits. Of course it depends too on what kind of nightcap you are talking about -- the drinking variety or the type that you wear on your head. The term "nightcap" also applies to the second game of a doubleheader (two games) in baseball.
For me, the answer to the original question would be that I've had a nightcap all my life. It actually belonged to my father before me and in this case he wore it to bed on cold winter nights. It wasn't just any kind of nightcap, it was the creation of my Aunt Hattie Sharpe and given to my dad as a Christmas gift. There was no front or back to the cap but the name "Ken" was embroidered in blue thread on what could naturally be assumed as the front, but it didn't matter when putting it on in the dark anyway.
There was no heat in the upstairs of our house in the 1930s and 40s and Ken had been complaining for some time that his bald head was cold at night in winter and while there were a lot of laughs when he opened his gift and promptly modelled it, he was extremely appreciative of his sister-in-law's thoughtful handiwork.
I have always prized that old nightcap that has survived 70 years (see photo) and have it displayed on a shelf in my office-den along with a lot of other family relics. Strangely, in my mind's eye, I always associate the nightcap with the parodied poem "The Night Before Christmas": "...Mamma in her kerchief and I in my cap, had just settled down for a long winter's nap..."
Strange as it may seem, there is comfort in this for me.
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