Background: Chronic wounds represent a persistent clinical challenge and impose a considerable burden on healthcare systems. These lesions often require multidisciplinary management due to underlying factors such as microbial colonization, impaired immunity, and vascular insufficiencies. Regenerative therapies, particularly autologous approaches, have emerged as promising strategies to enhance wound healing. Adipose tissue-derived stem cells (ADSCs) and platelet-rich plasma (PRP) may improve outcomes through paracrine effects and growth factor release. Methods: A prospective observational study was conducted on 31 patients with chronic wounds that were unresponsive to conservative treatment for over six weeks. Clinical and photographic evaluations were employed to monitor healing. All patients underwent surgical debridement, with adjunctive interventions—negative pressure wound therapy, grafting, or flaps—applied as needed. PRP infiltration and/or autologous adipose tissue transfer were administered based on wound characteristics. Wound area reduction was the primary outcome measure. Results: The cohort included 17 males and 14 females (mean age: 59 years). Etiologies included venous insufficiency (39%), diabetes mellitus (25%), arterial insufficiency (16%), and trauma (16%). Most lesions (84%) were located on the lower limbs. All patients received PRP therapy; five underwent combined PRP and fat grafting. Over the study period, 64% of the patients exhibited >80% wound area reduction, with complete healing in 48.3% and a mean healing time of 49 days. Conclusions: PRP therapy proved to be a safe, effective, and adaptable treatment, promoting substantial healing in chronic wounds. Autologous adipose tissue transfer did not confer additional benefit. PRP may warrant inclusion in national treatment protocols.