over shoes, over boots, phr. — Green’s Dictionary of Slang

over shoes, over boots phr.

also over the ankles

[? water pouring over the top of one’s footwear]

totally, recklessly committed.

1630		J. Taylor Works ii 145: For where true courage roots, the proverb says, Once over shoes, o’er boots [F&H].
1840		Marryat Poor Jack 360: Bessy’s in love right over the ankles.