What is Diamonds On The Soles Of Their Shoes?
1.
Absolutely filthy rich. From the Paul Simon song title from Graceland (1986).
Look at those nouveaux-riches types at the boarding school on sports day. They want everyone to know they have diamonds on the soles of their shoes.
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(n) An administrator of the typical sort, who rose to power more through ambition, aggression and connections than through skill, educat..