In recent years, the rate of caesarean sections has risen all over the world. Accordingly, efforts are being made worldwide to understand this trend and to counteract it effectively. Several factors have been identified as contributing to the selection of caesarean section (CS), especially an obstetricians’ beliefs, attitudes and clinical practices. However, relatively few studies have been conducted to understand the mechanisms involved, to explore influencing factors and to clearly define the risks associated with the caesarean section on maternal request (CSMR). This comparative study was conducted to elucidate the factors influencing the choice of CSMR, as well as to compare the associated risks of CSMR to CS for breech presentation among Italian women. From 2015 to 2018, a total of 2348 women gave birth by caesarean section, of which 8.60% (202 women) chose a CSMR. We found that high educational attainment, use of assisted reproductive technology, previous operative deliveries and miscarriages within the obstetric history could be positively correlated with the choice of CSMR in a statistically significant way. This trend was not confirmed when the population was stratified based on patients’ characteristics, obstetric complications and gestational age. Finally, no major complications were found in patients that underwent CSMR. We believe that it is essential to evaluate patients on a case-by-case basis. It is essential to understand the personal experience, to explain the knowledge available on the subject and to ensure a full understanding of the risks and benefits of the medical practice to guarantee the patients not only their best scientific preparation but also human understanding.