Though sleeping with a bra may not sound appealing to many women, some do it anyway in order to reap the benefits associated with this habit. Of course, there are pros and cons to this practice, and both should be considered before making a decision about it. The advantages of sleeping with a bra mainly apply to the use of special sleep bras, and include support for large breasts, modesty, and surgery recovery. The main disadvantage is the discomfort that wearing a bra to sleep may bring, especially since it has been found that this practice does not usually prevent sagging. Other disadvantages usually have to do with bras that are too tight, as they may cause problems in breastfeeding mothers in particular.

Many women who advocate sleeping with a bra use a sleep bra that lacks underwire, rather than a regular kind, as most women agree that the typical bra is too constricting to sleep in comfortably. Those who enjoy wearing the nighttime bra often claim that it makes it easy to change sleep positions without causing back pain. For example, sleeping on one side without a bra may be painful for women with large chests, so a sleep bra is often suggested to provide some support. Women who experience pain in their breasts due to menstruation or pregnancy hormones may also appreciate the extra support that sleeping with a bra can bring.

Additionally, many doctors suggest that patients wear some kind of binder at night after breast surgery. This can help protect the breasts from injury during the healing process, and also add support. While women who have undergone surgery may be required to sleep in a bra, others just prefer it for modesty's sake. For instance, women who live with other people or who are likely to be woken up in the middle of the night may like the extra coverage and support that a bra brings. It may also make them feel more comfortable when talking to others unexpectedly at night, such as in the case of emergency.

Women who are against sleeping with a bra on at night may point out that there is no evidence that wearing this garment to bed can prevent sagging. Instead, it often just makes women uncomfortable, without the promise of a perkier chest. In fact, many women wear ill-fitting bras, and sleeping with a bra that is too tight may lead to discomfort and serious medical issues. For example, breastfeeding women may find that wearing a bra to bed not only hinders milk production, but can also result in plugged milk ducts. This is often most easily avoided by skipping bras at bed altogether, though finding a sleep bra that fits well may also solve the problem.