Never made one, but I'd imagine it can be done. Would need some nifty wet moulding around the bowl if you weren't going for more of a smooth tapered look. I think my main concern, especially with a churchwarden, would be making sure that the long thin section is rigid enough to protect the stem from getting bent.
It may be easier to make a wooden liner.
Or you could make a wooden former to mould the leather round. I can recommend half tanned leather as it will thin and rigid at the same time.
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