Cryptic crossword clue
Well-heeled American should follow the Duke of Milan 10

The most common and most likely answer to this crossword clue is the 10 letter word PROSPEROUS

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Buddy explains!

The straight part
We know that "Well-heeled" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case well-heeled = prosperous.
The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does PROSPEROUS mean?

PROSPEROUS adjective
  1. Characterized by success
  2. Well off; affluent
  3. Favorable

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