* Fresh from the cobbler? (4-6)

I believe the answer is:

well-heeled

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'fresh' is the definition.
Both the definition and answer are adjectives. Perhaps there's an association between them I don't understand?

I don't understand how the rest of the clue works.

Can you help me to learn more?

(Other definitions for well-heeled that I've seen before include "Wealthy" , "Affluent" , "Prosperous, rich" , "Comfortably off" .)

I've seen this clue in the Sydney Morning Herald.

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