What is the connection between (a) successfully executing something tricky that not everyone could get away with, like an escape or an acrobatic maneuver or a daring sartorial fashion statement, and (b) removing by tugging, stripping, or peeling?
Rather than set it as a quiz and waiting for the answers to come in, let me just supply the following sentence that Daniel Deutsch saw in the New York Times:
With flowing black hair and a remarkable ability to pull off form-fitting black leather pants, Ms. Chang is a particularly glamorous ambassador of an art form not necessarily associated with lipstick and glitz.
Could the glamorous Ms. Chang really be noted for her prowess at tearing off her black leather pants? One assumes that only her most intimate friends would know how good she is at getting undressed; even a glamorous art ambassador — even Lady Gaga — doesn't customarily do that in public. (And Ms. Chang is not in the same area of the arts as Lady Gaga; she is a poet — Tina Chang, the poet laureate of Brooklyn.) So intended claim was surely the less dramatic one, illustrating not meaning (b) but merely meaning (a): that while you or I or the average poet might look silly in tight black leather pants, Ms. Chang succeeds in looking good in them.
But how remarkable it is that the writer chose the pull ___ off verb-preposition combination here without (one assumes) noticing the double entendre, and without the editors noticing it either. As I believe I may have said before, it is really remarkable how much polysemy and ambiguity we tolerate during every single minute we listen to our language — and how little regard utterers pay to the business of ensuring that the addressee will not misunderstand.