How long did it take for cobblers to make shoes in the middle ages?

From 3 to 6 months. A mold had to be taken of the feet of the person who ordered the shoes, the leather cut, and then sewn. Cobblers didn't premake shoes and often they were itinerant so they moved from place to place on a route. Today there are skilled crafts people who do make shoes the way they were made a 1000 years ago. Even today to get a pair of boots takes about 6-8 weeks from one of the modern cobblers.