Green’s Dictionary of Slang

1. (orig. US black) one who espouses the fashionable Bohemian stance of the period; the essence was a conscious downplaying of emotional display, a stance poss. facilitated by heroin addiction.

1938		Pittsburgh Courier (PA) 27 Aug. 11/1: The real sender came when he booted ‘After You’re Gone’ [...] I thought I was a hepster but I found myself padding the ground pads along with the rest.
1941		A. Lomax Mister Jelly Roll (1952) 233: Jelly Roll now had backing in his disputes with the ‘hipsters’ and ‘hot jive boys’.
1953		‘William Lee’ Junkie (1966) 57: A young Italian hipster named Ray used to come to the bar every day.
1959		W. Brown Teen-Age Mafia 15: Little brats who thought they were hipsters when they didn’t even know which end was up.
1961		T. Taylor Baron’s Court All Change (2011) 72: A genuine hipster of the female variety.
1965		L. Bruce How to Talk Dirty 5: My vocabulary [...] is usually flavored with the jargon of the hipster.
1973		E. Bunker No Beast So Fierce 85: I watched him depart [...] one arm swinging exaggeratedly, shoulders rolling in a hipster’s stroll.
1981		J. Ellroy Brown’s Requiem 72: ‘Shake it, daddy, what else do you want to know?’ he said. Besides suffering from terminal cancer, he was suffering from terminal hipsterism.
1998		P. Doyle (con. late 1950s) Amaze Your Friends (2019) 14: Max Perkal and his band of would-be hipsters [...] accounted for about seventy per cent of the total demand for Indian hemp.
1999		N. Cohn Yes We have No 31: He seems the complete jazz hipster, all grace and irony.
2000		Guardian Guide 19–25 Feb. 6: It’s a password to other hipsters that he has records by Chet Baker and Sonny Rollins.

2. in 21st century use, a liberal, culturally orientated youth cult for those under 30, often in creative occupations; seen as the current evocation of middle-class counter-cultural aspirations and fashions and praised or derided accordingly .

2007		in Urban Dict. 🌐 Hipsters a subculture of men and women typically in their 20's and 30's that value independent thinking, counter-culture, progressive politics, an appreciation of art and indie-rock, creativity, intelligence, and witty banter.
2012		M. Lacher On the Bro’d 87: [L]ong-haired, lame-ass annoying hipsters straight off planes from Brooklyn.
2016		Eve. Standard (London) 4 Apr. 44/3: The wiry, T-shirted creative has the look of a hipster.
2020		S.A. Crosby Blacktop Wasteland 202: A week ago, he was snorting coke off some hipster chick’s titty’.