Waggish describes someone who is silly and playful, and especially someone who displays a mischievous sense of humor. The word can also describe things that such a person might do or possess.

// He had a waggish disposition that could irk adults but typically delighted children.

// She denied the prank but did so with a waggish smirk that didn't match her disavowal.

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“[Patricia] Lockwood began her writing life quietly, as a poet. She found her first major audience on Twitter, posting self-proclaimed ‘absurdities’ ... that quickly came to define the medium’s zany, waggish ethos ...” — Alexandra Schwartz, The New Yorker, 25 Aug. 2025

One who is waggish acts like a wag. What, then, is a wag? It has nothing to do with a dog’s tail; in this case a wag is a clever person prone to joking. Though light-hearted in its use and meaning, the probable source of this particular wag is grim: it is thought to be short for waghalter, an obsolete English word that translates as gallows bird, a gallows bird being someone thought to be deserving of hanging (wag being the familiar wag having to do with movement, and halter referring to a noose). Despite its gloomy origins, waggish is now often associated with humor and playfulness—a wag is a joker, and waggery is merriment or practical joking. Waggish can describe the prank itself as well as the prankster type; the class clown might be said to have a “waggish disposition” or be prone to “waggish antics.”