Antonyms of adj well-heeled

1 sense of well-heeled

Sense 1
comfortable, easy, prosperous, well-fixed, well-heeled, well-off, well-situated, well-to-do -- (in fortunate circumstances financially; moderately rich; "they were comfortable or even wealthy by some standards"; "easy living"; "a prosperous family"; "his family is well-situated financially"; "well-to-do members of the community")

INDIRECT (VIA rich) -> poor -- (having little money or few possessions; "deplored the gap between rich and poor countries"; "the proverbial poor artist living in a garret")

Similarity of adj well-heeled

1 sense of well-heeled

Sense 1
comfortable, easy, prosperous, well-fixed, well-heeled, well-off, well-situated, well-to-do -- (in fortunate circumstances financially; moderately rich; "they were comfortable or even wealthy by some standards"; "easy living"; "a prosperous family"; "his family is well-situated financially"; "well-to-do members of the community")
       => rich (vs. poor) -- (possessing material wealth; "her father is extremely rich"; "many fond hopes are pinned on rich uncles")