Might mean (unverified): Display confidence and pride prominently.
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We found one dictionary that defines the word ride tall in the saddle:

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  1. ride tall in the saddle: Wiktionary

Definitions from Wiktionary (ride tall in the saddle)

verb:  (of a person) To ride a horse in an erect, imposing manner.
verb:  (idiomatic, by extension) To act or conduct oneself in a manner that is imposing, impressive, resolute, or manly.

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