Background and objectives: Total hip arthroplasty (THA) in obese patients (BMI > 30) is considered technically demanding, and it is associated with higher rates of general and specific complications including infections, component malpositioning, dislocation, and periprosthetic fractures. Classically, the Direct Anterior Approach (DAA) has been considered less suitable for performing THA surgery in the obese patient, but recent evidence produced by high-volume DAA THA surgeons suggests that DAA is suitable and effective in obese patients. At the authors’ institution, DAA is currently the preferred approach for primary and revision THA surgery, accounting for over 90% of hip surgeries without specific patient selection. Therefore, the aim of the current study is to evaluate any difference in early clinical outcomes, perioperative complications, and implant positioning after primary THAs performed via DAA in patients who were divided according to BMI. Material and methods: This study is a retrospective review of 293 THA implants in 277 patients that were performed via DAA from 1 January 2016 to 20 May 2020. Patients were further divided according to BMI: 96 patients were normal weight (NW), 115 were overweight (OW), and 82 were obese (OB). All the procedures were performed by three expert surgeons. The mean follow-up was 6 months. Patients’ data, American Society of Anesthesiologists (ASA) score, surgical time, days in rehab unit, pain at the second post-operative day recorded by using a Numerical Rating Scale (NRS), and number of blood transfusions were recorded from clinical charts and compared. Radiological evaluation of cup inclination and stem alignment was conducted on post-operative radiographs; intra- and post-operative complications at latest follow-up were recorded. Results: The average age at surgery of OB patients was significantly lower compared to NW and OW patients. The ASA score was significantly higher in OB patients compared to NW patients. Surgical time was slightly but significantly higher in OB patients (85 ± 21 min) compared to NW (79 ± 20 min, p = 0.05) and OW patients (79 ± 20 min, p = 0.029). Rehab unit discharge occurred significantly later for OB patients, averaging 8 ± 2 days compared to NW patients (7 ± 2 days, p = 0.012) and OW patients (7 ± 2 days; p = 0.032). No differences in the rate of early infections, number of blood transfusions, NRS pain at the second post-operative day, and day of post-operative stair climbing were found among the three groups. Acetabular cup inclination and stem alignment were similar among the three groups. The perioperative complication rate was 2.3%; that is, perioperative complication occurred in 7 out of 293 patients, with a significantly higher incidence of surgical revisions required in obese patients compared to the others. In fact, OB patients showed a higher revision rate (4.87%) compared to other groups, with 1.04% for NW and 0% for OW (p = 0.028, Chi-square test). Causes for revision in obese patients were aseptic loosening (2), dislocation (1), and clinically significant post-operative leg length discrepancy (1), with a revision rate of 4/82 (4.87%) during follow-up. Conclusions: THA performed via DAA in obese patients could be a solid choice of treatment, given the relatively low rate of complications and the satisfying clinical outcomes. However, surgical expertise on DAA and adequate instrumentation for this approach are required to optimise the outcomes.