With leggings on the market reflecting the size system of young women, they are not suitable for the changing body shapes of women in their 40s and 50s, and in the clothing industry, it is necessary to accurately ascertain the appropriate garment pressure for various body parts to increase customer satisfaction. This study thus aims to develop tight leggings suitable for middle-aged women by analyzing the quantitative values of garment pressure and performing a subjective evaluation of wearing by body part. The results showed that satisfaction was found to be high when the tilt angle of the back crotch line was increased. Meanwhile, the pressure at the rear waist point was minimal, or 0.00 kPa, indicating that the rear waist area was not as affected by pressure as other areas. However, the pressure at the mid-patella was found to be 2.48 kPa; at the tibiale, 2.09 kPa; and at the waist point, less than 0.98 kPa. Pressure stronger than that was found to cause discomfort as age increases due to a decrease in the maximum and average blood flow rates; however, for the lower leg area, it was found that high garment pressure had a positive effect on physical activity.