The term "well-heeled" is an American expression that dates back to the mid-1800s. As town cobblers made and repaired shoes, those who could afford the repair service and/or new shoes were considered well-heeled. Well-heeled is the opposite of the American expression "down at the heels" used in the seventeenth century. The heels on the shoes of the poor were often worn down and differed from those of the rich who were able to maintain their shoes or afford new shoes, while the poor could not.
Many people in the United States in the early 1800s went without shoes during the spring and summer and many others wore shoes only on special occasions such as church or school. Some children never even owned shoes until they were teenagers. By the mid-1800s shoe making became more industrialized and wearing shoes year round became more common.
Plimsolls were the first American rubber soled shoes and were made in the United States in the late 1800s. Humphrey O'Sullivan, an Irish-American, invented the rubber shoe heel and had it patented in 1899. Rubber soled shoes were promoted as "sneakers" by advertising agent Henry Nelson McKinney to accentuate the benefit of a quiet shoe as opposed to the usual noisy shoe.
Throughout the centuries, the expression well-heeled became more and more associated with the wealthy, the rich, and the concept of luxury. Well-heeled today means a person with the financial means to afford good quality shoes. Those with high earnings or high incomes can afford to be well-heeled in a variety of well-made shoes, so quantity as well as quality of shoes is often expressed by the term well-heeled.
Designer shoes, with their extravagant price tags, are marketed to the well-heeled shopper. Brands such as Gucci, Manolo Blahnik, and Prada start at about $400 for the most casual shoe and boots could cost up to $2,000 or more. Celebrities and the wealthy can afford the luxury, but designer shoes are out of range for the middle classes and below.
However, with the wide variety of inexpensive yet stylish shoes available today, most people can afford decent-looking shoes. Shoes are considered important to a person's image and job seekers are often encouraged by experts to be sure to have well-maintained, work-appropriate shoes. Second hand stores are often a good source for those who are not well-heeled financially, if the shoes are in good condition and just need a little polishing to make them look new.