The best time to buy a nursing bra is probably towards the end of pregnancy since the mother can get used to wearing the bra. It's recommended that nursing mothers not wear under wire bras and some women are very used to wearing under wire bras and so, I sometimes recommend that the mother start getting used to wearing a non-under wire bra in the last month of her pregnancy. It's also just more comfortable to find a good fitting bra that you have some room to grow and at the end of pregnancy because the rib cage is growing exponentially. It's helps to have a nice fitting nursing bra to use it postpartum.