Background and Objectives: Open fracture of the lower limb can lead to substantial bone and soft tissue damage, resulting in a challenging reconstructive scenarios, especially in presence of bone or periosteal loss, with a relevant risk of non-union. This work analyzes outcomes of using a double approach for orthoplastic reconstruction, adopting the free medial condyle flap to solve the bone defects, associated to a second free flap for specific soft tissue coverage. Indications, outcomes and reconstructive rationales are discussed. Materials and Methods: A retrospective investigation was performed on patients who underwent complex two-flap microsurgical reconstruction from January 2018 to January 2022. Inclusion criteria in this study were the use of a free femoral condyle periostal/bone flap together with a second skin-only flap. Only distal third lower limb reconstructions were included in order to help equalize our findings. Out of the total number of patients, only patients with complete pre- and post-operative follow-up (minimum 6 months) data were included in the study. Results: Seven patients were included in the study, with a total of 14 free flaps. The average age was 49. Among comorbidities, four patients were smokers and none suffered from diabetes. Etiology of the defect was acute trauma in four cases and septic non-union in three cases. No major complications occurred, and all flaps healed uneventfully with complete bone union. Conclusions: Combining a bone periosteal FMC to a second skin free flap for tailored defect coverage allowed achievement of bone union in all patients, despite the lack of initial bone vascularization or chronic infection. FMC is confirmed to be a versatile flap for small-to-medium bone defects, especially considering its use as a periosteal-only flap, with minimal donor site morbidity. Choosing a second flap for coverage allows for a higher inset freedom and tailored reconstruction, finally enhancing orthoplastic success.