[2] From 2013 to 2014, The Hairpin was edited by Emma Carmichael,[3] with Jia Tolentino as contributing editor.

[5][6] The site went on hiatus briefly but was revived in 2016 when Sylvia Killingsworth left The New Yorker to become editor of both The Awl and The Hairpin.

[8] The Hairpin had been home to several recurring features including Jia Tolentino's "Interview With a Virgin",[9] Jolie Kerr's "Ask A Clean Person",[10] former This American Life producer Jane Marie's makeup tutorial series "How To Be A Girl"[11] and Lindsay King-Miller's advice column "Ask A Queer Chick".

[12] Glen Weldon discussed the demise of The Hairpin as being in response to the decline in advertisement-driven website revenue, making a difficult situation for independent publishers.

The new owner, a Serbian DJ named Nebojša Vujinović Vujo, bought the site because it had "great reputation and excellent backlinks."