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From old + fashioned.[1] The cocktail (which goes back to at least the early 1800s) got its name in the late 1800s as more complicated cocktails became common and those who preferred simpler drinks began asking for old-fashioned cocktails.
Miss Menie, we should mention, has a commendable desire to sell her oldest-fashioned articles first; indeed, we believe that something of the sort has always been common among mercers. It is true, that the most conscientious of the trade make a point, in such cases, to say nothing of the fashionableness of the patterns, but in proportion to the care with which they do this, they enlarge on the good qualities of the texture and durability.
Pretty soon I struck into a sort of path[…]. It twisted and turned,[…]and opened out into a big clear space like a lawn. And, back of the lawn, was a big, old-fashioned house, with piazzas stretching in front of it, and all blazing with lights.
T. S. Eliot suspects Mr. Pound’s philosophy of being antiquated. W. C. Williams finds his “versification still patterned after classic metres”; and, apropos of ‘feminolatry,’ is not the view of woman expressed by the Cantos older-fashioned than that of Siam and Abyssinia? knowledge of the femaleness of “chaos”, of the “octopus”, of “Our mulberry leaf, woman,” appertaining more to the Grand Turk than to a Roger Ascham?
You can’t stay the night, because my parents are a bit old-fashioned.
1879, Albert Hastings Markham, “The Dutch Flag in the Northern Seas”, in Donald Macleod, editor, Good Words for 1879, London: Isbister and Company,, part I, page 95, column 2:
The people of Marken may almost be regarded as the oldest-fashioned in the world. They adhere to the same picturesque costume as was worn by their ancestors three hundred years ago, and their houses are built in the same primitive style as in those days.
It neither aims at, nor does it admit of, the gorgeousness of its predecessor; mainly, or at least partly, because it does not aim at or admit of that predecessor’s variety of rhythm. / In the respect with which alone we have to do, Steele is merely a more careless Addison, and Arbuthnot, in this as in others, is almost inseparable from Swift. Atterbury is slightly older-fashioned than the others, and nearer the Dryden group.
Bond took a shower and changed and walked down the road and had two Bourbon old-fashioneds and the Chicken Dinner at $2.80 in the air-conditioned eating house on the corner that was as typical of ‘the American way of life’ as the motel.
1996, Paul F. Boller, Presidential Anecdotes, page 286:
At the end of the workday, the Trumans liked to have a cocktail before dinner. Shortly after they moved into the White House, Mrs. Truman rang for the butler, Alonzo Fields, one afternoon and ordered two old-fashioneds.