playboy

American  

[pley-boi] / ˈpleɪˌbɔɪ /

noun

• playboys
  plural

1. a man who pursues a life of pleasure without responsibility or attachments, especially one who is of comfortable means.

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playboy British  

/ ˈpleɪˌbɔɪ /

noun

1. a man, esp one of private means, who devotes himself to the pleasures of nightclubs, expensive holiday resorts, female company, etc

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Other Word Forms

Noun Inflected Forms

• playboys
  plural

Etymology

Origin of playboy

First recorded in 1620–30; play + boy

Example Sentences

See Examples For:

playboy playboys

The 41-year-old royal misfit has long struggled with the monarchy's strictures, shaking off the angry young man and "playboy prince" tags only to find himself at loggerheads with his closest relatives.

From Barron's ● Aug. 23, 2026

Unlike the wealthy playboy Iron Man, the alien Superman, or the Amazon princess Wonder Woman, Spider-Man was created in 1962 to be relatable for comic book readers.

From The Wall Street Journal ● Jul. 30, 2026

It is about a con-man taking on the identity of a wealthy playboy.

From BBC ● Aug. 8, 2025

But since he was a young man, he has been obsessed with creating a macho image, inventing the persona of a high-flying playboy and king of the New York real estate world.

From Salon ● Jun. 20, 2025

You’re a failure, a playboy, a racetrack tout.”

From "A Confederacy of Dunces" by John Kennedy Toole

One wonders what he really thought about the pampered, preening, multimillionaire playboys of the contemporary global game, who change hairstyles weekly and win world championships sparingly.

From Los Angeles Times ● Dec. 29, 2022

Until his social media ban, Tate was operating something called Hustler University, which promised, for $49 a month, to turn his audience into rich playboys, as he presents himself to be.

From Salon ● Aug. 23, 2022

He spent the postwar years in Paris, befriending Prince Aly Khan and other jet-setting playboys who frequented casinos.

From Washington Post ● Jan. 11, 2022

They also need to shed any perceptions of the shoe as being for pretentious preppies, rakish playboys, or stuffy old men.

From The Wall Street Journal ● Aug. 31, 2016

He worships the vuvv playboys he works for.

From "Landscape with Invisible Hand" by M.T. Anderson