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What does rakish mean?

Looking for the meaning or definition of the word rakish? Here's what it means.

Adjective
  1. Dashingly, carelessly, or sportingly unconventional or stylish; jaunty; characterized by a devil-may-care unconventionality; having a somewhat disreputable quality or appearance.
  2. (dated) Like a rake; dissolute; profligate.
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Examples
The addition of a black leather flight jacket made him look like a particularly young and rakish test pilot.
His face has a slightly rakish quality to it, his eyes gleaming with charm, and cunning.
He propelled me to my brothers and left with a bow and a rakish grin towards me.
He arrives on the dot, his tall, dark-haired, slightly rakish figure hurrying up Petergate through the crowds.
With one or both side brims snapped up to the crown you get a rakish look which also stiffens the front brim against wind.
Cory shook his head at her, his blond fringe falling over his dark eyes, giving him the rakish look.

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