The story
From hip + -ster. First attested for someone carrying something on their hip in the U.S. in the 1920s. Attested as a variant of hepster in the 1940s, for a follower of the latest fashions/trends/styles.
First known use, by meaning
- from earlier 20th c. A person who is hip, being keenly interested in the latest trends or fashions.
- from earlier 20th c. A person who rejects mainstream culture; an anti-conformist.
Etymology from Wiktionary, CC BY-SA 4.0.