Well heeled is a phrase that describes a person who is prosperous or wealthy. There are several antonyms for well heeled, which means words that are opposite in meaning. Some of the antonyms for well heeled are destitute, impoverished, bankrupt, and needy. These words mean that someone is financially struggling, unable to make ends meet, and living in poverty. They lack the resources or wealth to live a comfortable life. Other antonyms for well heeled include broke, indebted, penurious, and insolvent. These words describe someone in a precarious financial situation that is unable to support themselves and may be facing financial ruin.