To set the measurements of bras for women in their 20s, considering the comfortableness in wearing and tightness, this paper conducted a questionnaire survey concerning breasts and bras as well as measurements of body and contact surface pressure. Easier and more accurate method of determining cup sizes based on the breast circumference is recommended to make up for the problem of current bra size system that can falsely measure cup sizes. Lower chest circumference was set at 5 cm equal intervals, and the breast circumference applicable to the cup size was set starting from the standard, 18 cm (A-cup), at 2 cm equal intervals, which gave the best coverage (88.1%).