"thinking cap" [antedated to 1827]

[Bonnie Taylor-Blake]

For its earliest example of "thinking cap," the OED shares one from
1846.  Here are some earlier examples.

-- Bonnie

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At dinner today I had a very free conversation with two intelligent
Virginians -- they assured me that the Jackson fever is burning out
fast -- that the old Dominion has at last got her thinking cap on and
the Tide of public opinion there is turning fast in favor of our
present Administration.  [From "Extract of a Letter, dated Washington,
Dec. 15," Sentinel of Freedom and New-Jersey Advertiser (Newark, NJ),
25 December 1827, p. 2; via Genealogybank.com.]

Uncle Ben was a thinking man.  He talked much about definitions, and
the nature of things, and moreover he was possessed of a very rare
instrument, caled a metaphysical diving bell by which he often
descented to the bottom and spent whole days and nights there, and
though he did not always bring up pearls; yet he always searched for
them.  Uncle Ben was mightily attached to his favourite instrument.
So much so, that he might be said to live in it.  This instrument
resembled very much what is called a thinking cap.  [From "From the
Philanthropist; Self Denial," The Maryland Gazette (Annapolis), 23
April 1829; p. 2; via Gale News.]

*Is Morgan murdered?*  Fools may ask such a question, when the whole
world acts upon the belief that he is and be scoffed at for their
folly; but fools sometimes ask questions, which cause the wise to put
on their thinking caps.  [From "From the Vermont Advocate," Boston
Masonic Mirror, 13 March 1830, p. 291; via ProQuest's American
Periodicals Series Online.]

If Miguel be not good, Pedro is no better and this our wise Ministers
will discover by and by, when they put off their fools, and put on
their thinking caps.  [From "Portugal," Westmoreland Gazette and
Kendal Advertiser (Kendal, Cumbria, England), 17 May 1834, p. 2; via
Gale News.]

If you will put on your thinking caps, and reflect a little, I believe
you will soon become wiser than your counsellors; but think you must,
before you vote.  [From "Democracy; To the Farmers and Working Men,"
Columbian Register (New Haven, CT), 4 October 1834, p. 2; via
Genealogybank.com.]

"Now, my boy, put on your thinking cap, (roared the witty Magistrate,
addressing Hob), and tell me why those individuals who are living in
Canada are like an inebriated man?"  [From "Waxiana," The Age
(London), 28 January 1838, p. 3; via Gale News.]

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