Background/Objectives: Poor nutrition in early life represents a relevant public health issue globally. The current study aimed to characterize eating habits among preschoolers and investigate the relationship with parents’ nutritional status. Methods: A secondary analysis of a cross-sectional study carried out at the Child Dentistry Clinics of the Istituto Stomatologico Italiano, Milan, Italy, including 171 patients aged 12–71 months and their parents, was conducted. Demographic data, anthropometric measurements, and information on children’s eating habits were collected. Results: The duration of exclusive breastfeeding was 5.9 (±6.8) months in 65% of children, and complementary feeding began at a mean (±SD) of 6.2 (±1.7) months in accordance with present recommendations. In contrast, the consumption of fruit juice 3.2 (±2.9) times/week, a protein intake of 3.0 (±0.6) g/kg, and a sugar intake of 20 (±8)% were over guideline limits. Overweight/obese children were introduced to cow’s milk earlier (p = 0.033) and consumed a higher percentage of total fats (p = 0.026) whilst consuming a lower percentage of carbohydrates (p = 0.050). In terms of children with both parents being obese or overweight, they consumed more carbohydrates (p = 0.048). Finally, we found that birth weight correlated positively with maternal BMI (ρ = 0.159; p < 0.05). The number of offspring correlated positively with the weekly frequency of sugar-sweetened beverage consumption before 24 months (ρ = 0.282; p < 0.001) whilst correlating negatively with the age of cow’s milk introduction (ρ = −0.226; p < 0.01). Conclusions: Our findings, according to recommendations, suggest that the prevention of obesity needs to begin in infancy. As parents play a pivotal role in establishing children’s food choices, nutritional education aimed at families is needed.
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