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Objectives: To use portable colorimetry to quantify color differences between facial skin and potential three head and neck microvascular free tissue transfer (MFTT) donor sites—radial forearm (RF), anterolateral thigh (ALT), and fibula (FF)—and compare these differences by pigmentation of the donor site skin and self‐identified race. Methods: In this cross‐sectional cohort study, healthy volunteers consented to handheld colorimeter measurements at the three potential MFTT donor sites (RF, ALT, FF) to quantify color match to the facial skin using the CIE color space (DeltaE). The comparison of ipsilateral to contralateral cheek served as control for measurements. Cross‐sectional measurements in healthy volunteers were then compared to measurements obtained in postoperative head and neck MFTT patients. Results: DeltaE measurements were obtained for 128 healthy controls and 24 postoperative patients (N = 152). With increasing lightness (decreased pigmentation) of the skin at the donor site, the color match significantly worsened (higher DeltaE) across all potential MFTT donor sites (all p < 0.05). DeltaE from healthy controls closely approximated postoperative color match measurements in patients who underwent cervicofacial MFTT (DeltaE RF: 5.3 vs. 6.0, p = 0.432; DeltaE ALT: 6.2 vs. 6.4, p = 0.822; DeltaE FF: 6.0 vs. 6.4, p = 0.806). Conclusion: Patients with decreased skin pigmentation who are undergoing head and neck MFTT may experience worse color discrepancy between cervicofacial skin and the transferred skin paddle than those with more pigmented skin. Portable colorimetry may identify patients who could benefit from interventions such as dermis‐resected free tissue reconstruction with skin grafting to improve postoperative appearance. Level of Evidence: 3 Laryngoscope, 134:3581–3586, 2024 [ABSTRACT FROM AUTHOR]