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Old Boots

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Like old boots. Famously, “Cheeky as old boots,” very saucy. “He ran like old boots,” i.e. very fast. The reference is to the nursery story of the Seven-leagued Boots, old being simply a word of fondness, as “Well, old boy,” etc. The allusion, suitable enough in many phrases, becomes, when used in slang, very remotely applicable.

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Entry taken from Dictionary of Phrase and Fable, edited by the Rev. E. Cobham Brewer, LL.D. and revised in 1895.

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Oignons dEgypte
Oil
Oil of Palms
Oil on Troubled Waters
Oil the Knocker (To)
Ointment
Olaf or Olave (St.)
Old Bags
Old Blade (An)
Old Bonâ Fide
Old Boots
Old Dominion
Old England
Old Faith Men
Old Fogs
Old Fox
Old Gentleman (The)
Old Glory
Old Gooseberry
Old Grog
Old Hands