The following illustrates the levels of late 14th c. English society between Baron and plowman. In general I have followed the ranks used in the 1379 Poll Tax, supplemented at the lower levels by the Sumptuary Laws of 1363. I have simplified some of the finer gradations of income in the 1379 law.
The ranks are illustrated by portraits from the Canterbury Tales, from the prologue unless otherwise noted. In many cases I have had to make educated guesses as to the wealth of the people described. Just how wealthy was the merchant or the prioress?
In some cases I have been guided by Russell’s Book of Nurture, a 15th century work on etiquette and manners. At dinner he would sit a prior with a knight, and so I have placed the prioress at that level. The monk is “to been an abbot able” but currently manages a cell, or subsidiary house, so I have placed him one level lower. The Wife of Bath is, or considers herself to be, the most substantial woman in her urban parish, and I have ranked her as a “sufficient merchant”
Chaucer doesn’t say what town the guildsmen, “shaply for to been an alderman”, are from. London aldermen were quite wealthy, with an implicit property qualification that was codified in the 15th c. as £1000 in goods or in money loaned out. This would suggest an income of over £100 a year. However, London aldermen were almost always from richer and more prestigious trades than Chaucer’s pilgrims. I suspect that they are either from a smaller town than London, or Chaucer is suggesting that they have an exaggerated sense of their own importance, or both.
Edith Rickert and other writers have noticed that Chaucer’s merchant corresponds in many details to Gilbert Maghfeld, a London merchant who handled goods worth £1,150 in 1390, and loaned money to Chaucer and many others. That would put him in the upper ranks of London merchants. Records from the Court of orphanage, 1350-1497, suggest a median estate of £200-£400, so even a more typical merchant would expect an income like a substantial squire.