Although vascularized lymph node transplantation (VLNT) has gained recognition as an effective treatment option for lymphedema, no consensus on the timing of transplant with other lymphatic procedures has been established. The aim of this study is to describe our institutional experience with VLNT, including our staged approach and report postoperative outcomes. A retrospective review of patients who underwent VLNT for upper extremity lymphedema from May 2017 to April 2022 was conducted. Patients were divided into fat- or fluid-dominant phenotypes based on preoperative workup. Patients with a minimum of 12-month follow-up were included. Records were reviewed for demographic, intraoperative, and surveillance data. Twenty-three patients underwent VLNT of the upper extremity during the study period, of which eighteen met the study criteria. Nine patients had fluid-dominant disease and nine patients had fat-dominant disease and had undergone prior debulking at our institution. Fluid-dominant patients demonstrated slight reductions in limb volume and hours in compression, and improvement in quality-of-life scores at twelve months. Fat-dominant patients who underwent prior debulking had a slight increase in limb volume without a change in hours of compression, and demonstrated improvements in quality-of-life scores in nearly all subdomains. Overall, 17% of patients discontinued compression therapy entirely. Improvement in extremity edema was present in 83% of postoperative MRIs. VLNT had varying effects on limb measurements while reliably improving quality-of-life and allowing for the potential of discontinuing compression. Utilizing a staged approach wherein debulking is performed upfront may be particularly beneficial for patients with fat-dominant disease.