Down at heel Definition 1 of 2Pro Tip 1/3Personal Appearance Used when someone's clothing or appearance suggests they have little money. His down at heel boots hinted at his financial struggles. Pro Tip 2/3Not Insulting While indicating poverty, it is descriptive and not meant as an insult. Despite his down at heel appearance, he carried himself with dignity. Pro Tip 3/3Subtle Judgement Can imply a fall from better circumstances or neglect of self-care. Once successful, the down at heel artist now wandered the streets.