Background: Parapneumonic pleural effusion (PPE) remains a relevant complication of pediatric pneumonia, with a substantial burden of morbidity, particularly in complicated forms. Optimal management strategies remain debated, with a recent shift toward more conservative approaches. Contemporary data on epidemiology, management practices, and outcomes are therefore needed. Methods: We conducted a retrospective cohort study of children admitted to our center with radiologically confirmed PPE between 2015 and 2025. Two study phases were defined to reflect the progressive shift in clinical practice: an interventional-prone period, in which complicated PPE (cPPE) was systematically drained, and a conservative period, in which drainage was reserved for patients with clinical deterioration. Data were compared between periods, and risk factors associated with pleural drainage during the conservative period were analyzed. Results: A total of 122 children with PPE were included (median age 4.1 years, 50% female), of whom 62.3% had cPPE. Pleural drainage was performed more frequently during the interventional period (55% vs. 24%). Patients managed during the conservative period had shorter duration of intravenous antibiotic therapy, shorter hospital stays, and faster radiological resolution, adjusting for disease severity. Within the conservative period, patients requiring pleural drainage (24.4%) had greater clinical and radiological severity, including higher rates of respiratory support and need for intensive care. Conclusions: In this cohort, the shift from a predominantly invasive to a more conservative strategy was not associated with worse clinical outcomes after adjusting for baseline severity. Pleural drainage was mainly reserved for patients with greater clinical compromise. These findings support a severity-guided approach to pleural drainage in pediatric PPE, in which conservative management with medical therapy alone may be safely considered in appropriately selected cases.