I'm not sure why you're having problems, but one of my characters has about five "repair items" on at any one time, and nothing is ever damaged or worn. He tends to hit things a lot, too, so something must be working.
This, in a way, though I got paranoid and end up trying to get every jewelery with the Repair Enchantment thinking 1, 2, or 3 of them isn't enough.
Try getting more items then just one with that effect.