Even being down one point will have a small chance of losing durability. But, by 20 or 30 points down, depending on tailor skill and whether you're doing it personally or with a deed, the chance becomes 100%.
Somewhere on here or in the Craftsman Forum (main or data chest subforum), there's actually the information on calculating the durability loss chance, but it was 3 or years ago, so I forget exactly where.