Crossword Genius

Opportunities to advance in stiff footwear? (4,4,5)

Ross

I believe the answer is:

dead mens shoes

I'm a little stuck... Click here to teach me more about this clue!

'opportunities to advance in stiff' is the definition.
I don't know anything about this answer so I can't judge whether it can be defined by this definition.

'footwear?' is the wordplay.
I cannot quite understand how this works, but
'footwear?' could be 'shoes' (I've seen this in another clue) and 'shoes' is present in the answer.
This may be the basis of the clue (or it may be nonsense).

Can you help me to learn more?

I've seen this clue in The Times and The Sunday Times.
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