Background: The 14-item version of the Oral Health Impact Profile (OHIP-14) has been widely used as a measure for oral health-related quality of life (OHQoL) since its publication in 1997. However, few studies have examined its psychometric properties and relationship with patient-reported oral health in pregnant women. Aim: To offer empirical evidence for appropriate use of the OHIP-14 among pregnant women in research and clinical practice. Objectives: (1) to empirically investigate the psychometric properties of the OHIP-14, (2) to modify it into the MOHIP-14PW (modified OHIP-14 for pregnant women), and (3) to compare their relationships with patient-reported oral health in pregnant women. Methods: In this real-world study (RWS) from suburban New York clinics, we collected OHIP-14 data from 291 pregnant women and assessed its psychometric properties at the item-, dimension-, and measure-level, including confirmatory factor analysis (CFA) and exploratory factor analysis (EFA). Accordingly, we modified the OHIP-14 into the MOHIP-14PW. Finally, we compared their correlations with patient-reported oral health scores. Results: All OHIP-14 items had severely skewed distributions, and two had a correlation with the patient-reported oral health < 0.1. All seven pairs of items correlated well (0.47 to 0.62), but the Cronbach’s alphas indicated suboptimal reliability, with two below 0.70. CFA results offered suboptimal support to the original structure, and EFA found a three-dimensional structure best fitted the data. Therefore, we modified the OHIP-14 into the MOHIP-14PW. CFA on the MOHIP-14PW offered stronger supports, and the Cronbach’s alphas increased to 0.92, 0.72, and 0.71. The MOHIP-14PW’s dimensions were more meaningful to pregnant women and had stronger relationships with patient-reported oral health than the OHIP-14; the average correlation coefficients increased by 26% from 0.19 in OHIP-14 to 0.24 in the MOHIP-14PW. Conclusions: The original OHIP-14 required modifications at the item-, dimension-, and measure- level, and the MOHIP-14PW had better psychometric properties, easier interpretation, and stronger correlation with patient-reported oral health in low-income pregnant women. Through an interdisciplinary RWS on a large sample of pregnant women, this study offers concrete empirical evidence for the advantages of the MOHIP-14PW over the original OHIP-14.