BACKGROUND: Female-to-male chest wall reconstruction is becoming more common, but while there is a growing body of the literature describing technique and algorithms, little detail is written on methods for creating a male appearing nipple areolar complex (NAC) from a female NAC utilizing free nipple graft techniques. Incorrect positioning of the NAC on the chest wall and suboptimal shaping and sizing of the NAC are common pitfalls in male NAC creation. METHODS: With this paper, we present techniques for nipple grafting to achieve improved male appearing NACs, as well as a simple, reproducible method for appropriate placement of the NAC relative to the borders of the pectoralis muscle. To validate our technique, we performed photographic analysis of 64 NACs in 32 volunteers with BMI of 25 or less. RESULTS: The anatomic study determined the cis-male nipple to be positioned on average 2.5 cm medial to the lateral border of the pectoralis muscle and 2.4 cm above the inferior pectoralis insertion. This supports our surgical technique of positioning the NAC in relation to the pectoralis borders rather than previously advocated anatomic landmarks. We also present reliable techniques for creating a round or horizontally oval final NAC shape as well as a composite grafting technique for cases of large papillae. CONCLUSIONS: Our anatomic study supports placement of the male NAC relative to lateral and inferior borders of the pectoralis muscle. Nipple grafting techniques presented allow for a simple and reproducible method of creating an aesthetic male NAC shape in female-to-male transgender chest reconstruction. LEVEL OF EVIDENCE IV: This journal requires that authors assign a level of evidence to each article. For a full description of these Evidence-Based Medicine ratings, please refer to the Table of Contents or the online Instructions to Authors www.springer.com/00266 .