Objectives: To determine if breastfeeding and its duration are associated with a reduced risk of obesity among Kuwaiti preschool children. Subjects and Methods: The sample consisted of 2,291 (1,092 males and 1,199 females) preschool children (3–6 years of age) and their mothers. The data were collected from September 2003 to June 2004. Height and weight measurements were used for defining weight status while other data were collected by questionnaire. Results: There was no significant association of breastfeeding or its duration with either overweight or obesity among preschool children after adjusting for effects of the confounders. The child’s gender, age and birth weight were the significant factors influencing current weight. Girls were at 32% higher risk of becoming obese than boys. Children aged 4–5 years were at nearly 3 times higher risk of overweight and obesity than children of less than 4 years. Children with higher birth weight (≥4 kg) had double the risk of obesity than those of normal birth weight (≥2.5 to <4.0 kg). Maternal obesity was a strong predictor of obesity in the children. A child with an obese mother had nearly 2 times higher risk of being overweight (BMI between the 85th the 95th percentiles) and 3 times of being obese (BMI ≥95th percentile) compared to a child born to a mother with a normal body weight. Conclusion: Breastfeeding and its duration are not associated with obesity status. However, there is a positive association between child and maternal obesity.