(1) Background: The role of the umbilical scar and its repositioning remains one of the most important surgical steps in the execution of any type of abdominoplasty, including those involving “inverted-t” or “fleur de lys” incisions. A consequence of this is a surgeon’s Hamletic dilemma: to keep or not to keep the original umbilical scar? (2) Methods: A retrospective observational study was conducted on all patients undergoing “T-inverted” abdominoplasty at the Department of Plastic Surgery of the Santa Maria alle Scotte University Hospital, Siena, between January 2018 and December 2020. Twelve months after the surgery we submitted to all patients the U-score questionnaire about their feelings about their umbilicus’s appearance. Patients could assign a score from 1 (very dissatisfied) to 4 (very satisfied) to each of the five items of the score. (3) Results: The average of the scores attributed by the nine patients in whom the navel was preserved is 13 (Range 10-17), while in patients on whom a navel reconstruction was performed, the mean score is 16.8 (Range 12-20). The mean score of patients with a reconstructed umbilicus is, therefore, statistically higher than that of the other group of patients (-value = 3.88, = 0.000374) with an average increase of 3.8 points. (4) Conclusions: We can state that the reconstruction of a new navel is the right answer to the Hamletic dilemma in patients having undergone vertical or anchor abdominoplasty.