The best time to purchase a breastfeeding bra is during the late stages of pregnancy. This is usually around the time when pre-pregnancy bras begin to become somewhat uncomfortable. Look for a breastfeeding bra that gives good support and allows plenty of room for nursing pads. Buy at least three to four good breastfeeding bras. When you are nursing, you will likely leak some breast milk. Because of that, always keep an extra breastfeeding bra handy.