Etymology

rakish

R1A1K5I1S1H4

Today it means: Dashingly, carelessly, or sportingly unconventional or stylish; jaunty; characterized by a devil-may-care unconventionality; having a somewhat disreputable quality or appearance. Full definition →

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The story

From rake (“man habituated to immoral conduct”) + -ish.

Etymology from Wiktionary, CC BY-SA 4.0.