Approximately 23% of preschoolers are overweight or obese. Establishing a healthy dietary lifestyle at an early age can improve later child diet and body weight. This study examined the determinants of past infant feeding practices that do not follow standard feeding recommendations (breastfeeding for less than 6 months duration, cow's milk prior to the first year of age and solid foods at or before 4 months of age). It also examined the role of parental perception of child weight in the first 2 years-of-life on past infant feeding practices as well as current child diet and body weight. Families of 497 preschoolers aged 22-63 months (39.0 ± 8.2) were recruited from 30 child care centers in East-Central Illinois. Main findings indicate that past infant feeding practices were common and varied by socio-demographic factors including race/ethnicity, parental education and child gender. Children perceived as overweight in the first 2 years-of-life tended to breastfeed for lesser duration. Additionally, the majority (79.8%) of preschoolers who were classified as overweight using BMI percentile were perceived as non-overweight by the parent in the first 2 years-of-life. Mean daily total fatty/sugary food intake was higher among those perceived to be non-overweight in the first 2 years-of-life. These findings have identified parental perception of child weight in the first 2 years-of-life as a modifiable risk factor for unhealthy child diet and obesity among preschoolers.