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It comes from "plain vanilla", at least down here in South Texas. Add something to "plain vanilla" ice cream, like strawberries or peanut butter, and you don't have "plain vanilla" ice cream anymore, now do ya?
Now, as for "plain Jane", I'm not sure how that one originated...
Lets see if we can track down the first use next ;-)
I remember first coming across it in the late 80s with "vanilla amiga" meaning an out-the-box one with no extra memory etc. (yes, it was used for hardware too ;-)
Hmmm. Well, I'm 56. I've been using "it's a vanilla *whatever's the thing under discussion*" since I was about 14 or so.... which would be 1961. Besides old, what does that make me - the originator of the usage? Not likely....
Says that ice cream was invented some time after 1553 (I know it talks about Marco Polo, but alot suggests he was lying about his journeys) so, that gives us a rough estimate of the time.
After 1700 it seemed to raise in popularity, but in 1800 is when other flavors started coming out.
So we know it's younger than 204 years old.
And I actually managed to find this page on vanilla etymology (I only spent two minutes on this - it was the first query I entered!):