Background: More epidemiological data about lentigo maligna melanoma (LMM) are required to define follow-up guidelines. The study focused on recurrence, progression, and overall survival of LMM managed with primary wide local excision. Methods: In a 23-year retrospective study (1994 to 2016), a cohort of patients with LMM was evaluated by collecting data about the tumor location, the Breslow depth, the presence of ulceration, and patients’ age and sex. Local recurrences, locoregional and distant metastases, and disease-free and overall survival were additionally assessed. Results: Overall, 150 cases (84 male, 66 female, mean age 71.3 ± 11.3 years) of single, localized, primary LMM with a mean follow-up of 6.6 ± 4.4 years were included. A total of 33 (22.2%) patients underwent sentinel lymph node biopsy (SLNB) during surgical excision. However, positive SLNB was detected in none of them. The multivariable Cox analysis indicated that age of diagnosis and male gender significantly influenced the overall survival, while a shorter disease-free survival could be correlated with a greater Breslow thickness. The metastatic potential turned out to be low, entailing 7 deaths in the context of the LMM. Conclusion: Male gender, age over 70 at diagnosis, and a Breslow thickness greater than 0.75 mm were associated with a statistically significant decrease in overall disease-free survival in the current study. The results of the study confirm the favorable outcome of LMM. However, diagnosed patients should undertake regular follow-ups. The intensity of follow-up in these patients can be individualized based on the probability of recurrence/metastasis and overall survival. Furthermore, the study showed that SLNB might not be a necessary staging procedure in patients with LMM.