Though the Romans of old said calceus urit, they meant it physically, the shoe or sandal frets or pinches.
However, the figurative sense of the expression “to know where the shoe pinches”, where hardship occurs or difficulty lies or trouble may be experienced, has been in English usage for at least six centuries.
Chaucer had it in Canterbury Tales (c. 1386) when, in “The Merchant’s Tale,” he has the merchant’s brother say:
“Myn neighebours aboute
Sayn that I have the moste stedefast wyf,
And eek the meekest oon that berith lyf;
But I woot best (know best), wher wryngith (pinches) me my scho.”
The French phrase, a direct transalation, is c’est la que le soulier me pince, though c’est la que le bat me blesse, literally, “that’s where the saddle galls me,” is heard more frequently.
Germans say, wissen wo einen der Schuh druckt, “to know where the shoe pinches one.” Spaniards say, Cada uno sabe donde le aprieta el zapato, “Each one knows where the shoe pinches him.”