behaving and dressing in a way that is confident and slightly unusual, but attractive
Origin and usage
The adjective rakish comes from the noun ‘rake’ and the suffix ‘ish’. It was first used at the end of the 17th century.
Rakish derives from the noun rake, which refers to a man who behaves immorally; the life of such a man was depicted in a famous series of paintings by the 18th century painter Thomas Hogarth called A Rake‘s Progress. This meaning of ‘rake’ has no connection with the garden tool, which comes from Germanic. Rather, it may be related to another meaning which refers to the way a ship projects beyond its keel at the front and back. This noun has a related adjective meaning ‘suggesting speed’, which was added to the Open Dictionary in 2010. Back to the main meaning: in this meaning rakish collocates with nouns including charm, smile and good looks, as well as ‘hero’. It is often found in the phrase ‘at a rakish angle’ meaning tilted, generally in reference to how a hat is worn. This ‘angled’ sense may have been influenced by the ‘ship’ meaning, although a rakish man might well wear a hat at a rakish angle to advertise his rakishness. The related adverb is rakishly. This collocates with ‘handsome’, as well as occurring in phrases describing how something is angled, as in the last quotation below.
“The Country Wife paints a picture of a rakish hero named Horner, who regularly brags, cheats and lies to seduce the wives and daughters of London’s most prominent businessmen.”
“Smoky swaggered in – a muscular wiry man of about 5′ 8″, wearing a hat tilted at a rakish angle.”
“Wearing his flight helmet rakishly askew, looking more the politician than the former sailor, he’s piped aboard with a time-honored bosun’s whistle.”
bold, breezy, jaunty, raffish, self-assured