This study investigated differences in standard measurements used to determine bra size, under-bust chest circumference (UBCC) and over-bust chest circumference (OBCC), measured from a three-dimensional scan (hand-held scanner) compared to the direct measurement in 111 women (age 21–56 years; right breast volume 57–1672 mL; bra size 10A–18G). Bland–Altman plots of UBCC measurements showed a large positive bias and wide limits of agreement (12 cm; −4.6 to 28 cm), which increased as band size increased but decreased when the breasts were digitally removed from the scan prior to the UBCC measurement. The difference in UBCC measurements determined from scans compared to direct measurement had a strong positive correlation with breast volume and breast ptotis. The OBCC measurements showed a small positive bias (2.4 cm; −3.4 to 8.4), consistent across the range of bra sizes. Bra band size measurements determined from three-dimensional scans can be inaccurate in women with large, ptotic breasts. Practitioner Summary: We investigated potential errors in anthropometric data derived from three-dimensional scans used for bra design and fit. Bra band size measurements taken from three-dimensional scans were over-estimated in women with large breasts, whereas bra cup size measurements were accurate to within one-cup size across the entire range of bra sizes.