Introduction: Esophagectomy for esophageal cancer traditionally involves delayed postoperative oral feeding due to concerns about complications like anastomotic leakage. Enhanced Recovery After Surgery (ERAS) protocols favor early oral feeding (EOF), but its safety and benefits remain debated. This systematic review and meta-analysis compared EOF versus late oral feeding (LOF) after esophagectomy. Methods: We systematically searched PubMed, Scopus, Web of Science, EMBASE, and the Cochrane Library through March 2025 for primary studies comparing EOF (≤7 days post-op) with LOF (>7 days or delayed) in adult patients after esophagectomy. Outcomes included anastomotic leakage, pneumonia, other complications, gastrointestinal recovery, length of hospital stay (LOS), quality of life (QoL), and mortality. Results: Twenty-nine studies involving 3962 patients were included. There was no significant difference in the risk of anastomotic leakage between the two groups (RR: 1.03, 95% CI: 0.80–1.33, p = 0.82, I² = 0%). EOF was associated with a significantly shorter time to first flatus (Cohen’s d: −1.26, 95% CI: −1.93 to −0.58, p < 0.001) and first defecation (Cohen’s d: −0.87, 95% CI: −1.51 to −0.22, p = 0.01) and a shorter LOS (p = 0.01). No significant differences were found for other complications (acute respiratory distress syndrome [ARDS], chyle leak, conduit issues, ileus, sepsis, wound infection) or mortality rates (in-hospital, 30-day, 90-day, overall). QoL assessment suggested potential improvement in emotional function with EOF. Conclusions: EOF after esophagectomy appears safe, as it does not increase the risk of anastomotic leakage or other major complications compared to LOF. It is associated with faster gastrointestinal recovery and shorter hospital stays, supporting its use within ERAS protocols.