Introduction In this article, we present the Canadian Dermatology Association’s (CDA) Choosing Wisely Canada (CWC) list of top “Five Things Physicians and Patients Should Question in Dermatology” and the evidence in support of each recommendation. Methods Using a nominal technique, the CDA Working Group and Task Force generated an initial list based on literature review and expert consultation. After several rounds of list refinement via a modified Delphi process, a final list of recommendations was generated. These were approved by the CDA Board of Directors, presented at the CDA 93rd Annual Conference in 2018, and published by CWC in 2019. Results The top five recommendations are as follows: (1) Don’t routinely prescribe antibiotics for bilateral lower leg redness and swelling; (2) Don’t routinely prescribe topical combination corticosteroid/antifungal products; (3) Don’t routinely use topical antibiotics on a surgical wound; (4) Don’t prescribe systemic antifungals without mycological confirmation of dermatophyte infection; and (5) Don’t use oral antibiotics for acne vulgaris for more than 3 months without assessing efficacy. Discussion This list of recommendations aims to encourage both physicians and patients to reevaluate ineffective, yet common, practices in treating dermatologic conditions. These recommendations represent actionable changes in practice, and therefore have considerable potential to enhance value-based care in dermatology. Conclusions This list was developed to identify tangible changes in practice within dermatology that may reduce inefficiencies, prevent potential patient harm, and improve care. Future advocacy work may include updates, feedback obtainment, and patient care handouts, to continue to promote value-based healthcare and best practices.