Breast cancer requires complex clinical care. Well-being is an intricate concept, encompassing physical, functional, emotional, and social aspects. Background: This study aims to evaluate the relationship between the type of surgery our patients underwent and the timing of the reconstructive surgery with physical, emotional, social, and functional well-being. Furthermore, through our research we tried to identify potential mental health comorbidities in patients with breast cancer, clinical symptoms, and well-being in women with breast cancer, depending on the type of required surgery. Methods: The study included 69 women diagnosed with breast cancer, in stages I to III, divided in two groups: I—patients with oncoplastic breast-conserving surgery and contralateral correction surgery, for symmetry reasons; II—patients who underwent modified radical mastectomy and late breast reconstruction with contralateral symmetrisation. We evaluated socio-demographic aspects, alongside depression, anxiety, stress (DASS 21), and well-being (FACT-B). Data were statistically processed; statistical significance was set at p < 0.05. Results: Clinical elements of depression, anxiety, and stress were noted in both groups, without statistical significance (p > 0.05). Significant differences were found regarding psycho-emotional (p = 0.035) and functional well-being (p = 0.001), with higher scores for group I. The chi-square test indicated statistically significant differences (at p < 0.01) between the groups, regarding the frequency of scores on items B4 and B9 (FACT-B items, related to feminine aesthetics and desirability), with evidently higher scores in group I than in group II. Conclusions: The state of well-being, as well as the items related to femininity and sexuality had higher values in the group of women treated by oncoplastic conservative surgery compared to late reconstruction after modified radical mastectomy.