Microsurgical breast reconstruction demands the highest level of expertise in both reconstructive and aesthetic plastic surgery. Implementation of such a complex surgical procedure is generally associated with a learning curve defined by higher complication rates at the beginning. The aim of this study was to present an approach for teaching deep inferior epigastric artery perforator (DIEP) and transverse upper gracilis (TUG) flap breast reconstruction, which can diminish complications and provide satisfying outcomes from the beginning. DIEP and TUG flap procedures for breast reconstruction were either performed by a senior surgeon (>200 DIEP/TUG, ”no-training group”), or taught to one of five trainees (>80 breast surgeries; >50 free flaps) in a step-wise approach. The latter were either performed by the senior surgeon, and a trainee was assisting the surgery (“passive training”); by the trainee, and a senior surgeon was supervising (“active training”); or by the trainee without a senior surgeon (“after training”). Surgeries of each group were analyzed regarding OR-time, complications, and refinement procedures. A total of 95 DIEP and 93 TUG flaps were included into this study. Before the first DIEP/TUG flap without supervision, each trainee underwent a mean of 6.8 DIEP and 7.3 TUG training surgeries (p > 0.05). Outcome measures did not reveal any statistically significant differences (passive training/active training/after training/no-training: OR-time (min): DIEP: 331/351/338/304 (p > 0.05); TUG: 229/214/239/217 (p > 0.05); complications (n): DIEP: 6/13/16/11 (p > 0.05); TUG: 6/19/23/11 (p > 0.05); refinement procedures (n): DIEP:71/63/49/44 (p > 0.05); TUG: 65/41/36/56 (p > 0.05)), indicating safe and secure implementation of this step-wise training approach for microsurgical breast reconstruction in both aesthetic and reconstructive measures. Of note, despite being a perforator flap, DIEP flap required no more training than TUG flap, highlighting the importance of flap inset at the recipient site.