Lipedematous scalp (LS) and lipedematous alopecia (LA) are uncommon dermatological conditions characterized by lipid accumulation within scalp tissue, leading to a thickened and boggy scalp. While the exact cause remains elusive, these conditions are believed to be on a spectrum of the same underlying disease process. LS/LA patients can experience dysesthesia of the scalp, but LA is associated with additional hair growth abnormalities. The pathogenesis remains poorly understood, with some cases suggesting a link to hormone leptin dysregulation and/or hyperlipidemia. We present a 73-year-old African American female with a medical history of hypertension, hyperlipidemia, and partial thyroidectomy who presented to the clinic with a two-week history of an itchy, burning 'rash' on the scalp. Physical examination showed normal hair density, but palpation revealed scalp edema and diffuse bogginess. While blood tests were mostly normal, she had an elevated antinuclear antibodies (ANA) titer (1:160). A punch biopsy revealed lichenification, but subsequent non-contrast magnetic resonance angiography (MRA) showed increased scalp fat tissue measuring up to 11 mm, confirming the diagnosis of LS. The patient was reassured that this finding was benign; however, she continued to experience dysesthesia. Our patient experienced minimal relief with topical steroids, leading to the consideration of intralesional steroid injections. The case highlights the importance of recognizing and managing LS as a distinct dermatological entity that requires further research to elucidate underlying mechanisms and establish standardized treatment protocols for this condition.