fling (one's) cap over the windmill

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fling (one's) cap over the windmill

To act in a deranged, reckless, or unconventional manner. Refers to the eponymous character of the novel Don Quixote, who tosses his hat over a windmill (which he imagines is a giant) as a challenge to it. Sarah is always trying to buck social conventions, flinging her cap over the windmill whenever possible. I know you like to take risks in business, but don't fling your cap over the windmill.
See also: cap, fling, over, windmill

fling (or throw) your cap over the windmill(s)

act recklessly or unconventionally. dated
1933 John Galsworthy One More River I suggest that both of you felt it would be mad to fling your caps over the windmill like that?
See also: cap, fling, over, windmill