If someone says that you are well heeled then you should take it as a compliment, meaning as it does that you are either well educated, or well brought up, of good stock, in a good position and generally showing positive sentiments.
The origin of this ophrase is to do with the cockfights, and not the fashion of our ancestors as some might believe.
It comes from the fact that they would have spurs added to them when fighitng to help them out, and a pair that had good heels was well heeled and they would win as a result. And hence the phrase of being well heeled came in as associated to someone liked with money and well positioned and looking good.
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