Objective The objective of this study was to determine whether anthropometric measurements such as head circumference (HC), body mass index (BMI), and body surface area (BSA) can predict car seat tolerance screen (CSTS) failure. We hypothesized that subjects with larger HC and lower BMI/BSA would have increased risk of failure. Study Design We performed retrospective medical record review of infants born in 2013 who qualified for CSTS due to being born preterm (< 37 weeks) or low birth weight (LBW). We performed bivariate analyses of clinical and demographic risk factors including anthropometrics to identify predictors of CSTS failure. Results In this study, 19 of 366 subjects failed their CSTS (5.3%). There were no significant differences in HC, length, BSA, BMI, or ratio of HC to length, BMI, or BSA between those who passed versus failed. On subgroup analysis of preterm infants, the significant predictor of failure was multiple gestation (p = 0.024). In the term LBW cohort, requiring nasal canula (NC) (p = 0.03) and having limited or no prenatal care (PNC) (p = 0.0006) were both significant predictors of failure. Conclusion Neither absolute measurements nor the ratios of HC to body measurements predicted CSTS outcome. Multiple gestation was a significant predictor of failure in preterm infants, while NC requirement and poor PNC were predictors in LBW term infants.