Green’s Dictionary of Slang

1. (orig. US) the very best, the finest example.

1893		P.H. Emerson Signor Lippo 53: Yes, clever pip.
1901		Marvel XV:389 Apr. 11: ‘Great pip!’ yelled the unfortunate proprietor.
1919		D. Runyon ‘A Tale of Two Fists’ XXIV in Pittsburgh Press (PA) 8 June 27/8: ‘Say, she was a pip’.
1921		Jerry on the Job [comic strip] Here’s a pip of a story about capital punishment.
1928		J. Callahan Man’s Grim Justice 139: I’ve got to make that dame [...] She’s a pip.
1938		J. Weidman I Can Get It For You Wholesale 222: Not only were the dresses pips, but the idea of getting the chorus of a musical comedy to wear them had caught on.
1940		F.S. Fitzgerald ‘Pat Hobby’s Secret’ in Pat Hobby Stories (1967) 75: My idea was a pip.
1945		(con. 1941) R. Westerby Mad in Pursuit 239: The Dunkirk Mothers’ stories were a pip.
1952		Lait & Mortimer USA Confidential 34: Now comes the pip! [Ibid.] 93: Queers are not only swell prospects for dope but are pips to put the blackmail bite on. [Ibid.] 224: Pittsburgh is in a pip of a position with Federal patronage.
1958		Dly Mirror 12 June 12/2: It’s toodle-pip soon to this pip of a girl.
1965		(con. 1930s) R. Wright Lawd Today 152: Boy, you should have heard the speech the Governor handed out last week. It was a pip!
1975		L. Rosten Dear ‘Herm’ 180: Well, pal, here’s a pip!
1990		Stage (London) 16 Aug. 67/1: Carl Brent [...] comedy impresionist; his Norvelle’s a corker; Presley’s a pip.
2000		(con. 1968) Guardian Weekend 13 May 35: He’s a popeye, he’s a panic, he’s a pip.

2. (US) a negative, bad example.

1900

E.H. Babbitt ‘College Words and Phrases’ in DN II:i 49: pip, n. A pippin.

3. (US) an innocent.

1926		J. Tully Jarnegan (1928) 154: She was a pip [...] and she looked clean – like a new cake of drug-store soap.
1934		‘Jiggs in “Phew”’ [comic strip] in B. Adelman Tijuana Bibles (1997) 15: You’re a pip Janey! You’d better keep away from New York [...] Somebody would sell you the Brooklyn Bridge.

4. an attractive woman.

1919		Washington Times (DC) 31 Dec. 10/5: [cartoon caption] Ah — some pip strolling along the Park wall there — wonder if I can make it a twosome...
1932		W.R. Burnett Giant Swing 99: ‘What a pip she is! What hair! The real stuff; no henna to that head of hair. And what a pair of pins!’.
1941		‘Digg Mee’ ‘Observation Post’ in N.Y. Age 18 Jan. 10/4: If you’re looking for a gal [...] just take my tip and you’ll get a ‘pip’.
1953		A.J. Liebling Honest Rainmaker (1991) 111: The girls were pips.
1956		T. Thursday ‘Dead Men Don’t Move’ in Smashing Detective Stories Jan. 🌐 She appeared to be in her fading forties—though she must have been a pip up to, say, thirty-five.