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The search for a perfect-fitting bra that also complements the look you're going for may seem never-ending. But truly, the healthiest bra to wear is the one that feels most comfortable and is actually your size. According to a 2008 study performed at Victoria University in Melbourne, Australia, 80 percent of people who wear them wear the wrong bra size on a daily basis. Furthermore, Dr. Teplinsky notes, some people have asymmetric breasts. "[These people] may benefit from a specialized fitting, which can place extra padding on one side and avoid overcompression on the other side," she says.