Background: Diffuse dermal angiomatosis (DDA) is a rare, reactive vascular disorder of the skin. Association with vascular disease, smoking, and large pendulous breasts has been reported. No standard of care exists but benefit with medication and reduction mammaplasty has been reported. Methods: We report a case of a 49-year-old obese female with a history of smoking who presented with DDA that improved with smoking cessation and pentoxifylline prior to reduction mammaplasty. We also performed a retrospective chart review of all patients with DDA seen at our institution between 2010 and 2020. Results: Eight female patients with DDA affecting the breasts were evaluated at our institution. The mean age was 49.5 years. Five of the patients noted symptoms at presentation. Obesity was seen in 7 (87.5%) patients and 5 (63%) had a smoking history. There was no significant difference between symptomatic and asymptomatic groups in regard to age, t4=-0.63, p=0.56, but BMI trended higher in the symptomatic group, t6=2.27, p=0.06. Three patients (38%) were noted to have fibromyalgia. All symptomatic patients saw improvement in their symptoms with treatments including reduction mammaplasty (1 patient), aspirin (1 patient), pentoxifylline (3 patients), smoking cessation (2 patients), and/or weight loss (1 patient). Conclusions: Our series is the second largest series of DDA of the breasts and confirms many reported associations including obesity, smoking, and large pendulous breasts. We report the first known case of improvement with weight loss as a sole intervention, as well as identify a novel potential association between DDA and fibromyalgia.