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This story begins, randomly, with ships.

In the past, the appearance of the ship upon its return would serve to indicate how it fared at sea. This would effectively mean that those that were victorious on an encounter with an enemy ship would sail into port with flags flying from the mastheads whereas those that were defeated (assuming, you know, they could still sail) used to “strike their colors” (which is a fancy way of saying they took the flag down. In this example colors = flag) to signify their defeat.

So essentially if you “pass with flying colors” you succeeded.

These phrases were really only used as nautical terms for a long time until some time after the 18th century when they became figurative talk. There is also another phrase like this, that is way less used, to “go down with flying colors” (or come through with) which basically means to commit.

Basically, a lot of phrases involving colors are flag related “show your true colors”, for instance, which referred to the fact that a lot of ships kept the flags unfurled.

Flags and ships! Who would’ve known?