Here is a seemingly simple problem from Futility Closet.
“A quickie from Peter Winkler’s Mathematical Puzzles, 2021: Can West Virginia be inscribed in a square? That is, is it possible to draw some square each of whose four sides is tangent to this shape?”
Technically we might rephrase this as, can we inscribe a flat map of West Virginia in a square, since the boundary of most states is probably not differentiable everywhere, that is, has a tangent everywhere.
But the real significance of the problem is that it is an example of an “existence proof”, which in mathematics refers to a proof that asserts the existence of a solution to a problem, but does not (or cannot) produce the solution itself. These proofs are second in delight only to the “impossible proofs” which prove that something is impossible, such as trisecting an angle solely with ruler and compass.
Here is another classic example (whose origin I don’t recall). Consider the temperatures of the earth around the equator. At any given instant of time there must be at least two antipodal points that have the same temperature. (Antipodal points are the opposite ends of a diameter through the center of the earth.)
See Existence Proofs (revised)
(Update 10/2/2021) I fixed a minor typo: “tail” should have been “head”

Here is a slightly different kind of problem from the Polish Mathematical Olympiads.
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Here is a challenging problem from the Polish Mathematical Olympiads published in 1960.
Here is another Brainteaser from the Quantum magazine.
This is another simple problem from Five Hundred Mathematical Challenges:
This problem comes from the Scottish Mathematical Council (SMC) Senior Mathematical Challenge of 2008:
Again we have a puzzle from the Sherlock Holmes puzzle book by Dr. Watson (aka Tim Dedopulos).
Ian Stewart has a nice logic problem in his Casebook of Mathematical Mysteries, which includes a pastiche of Sherlock Holmes in the form of Herlock Soames and Dr. Watsup, along with brother Spycraft and nemesis Dr. Mogiarty.