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Background/Objectives: To investigate whether chronic cosmetics use near or directly on the eyelid margin contributes to tear film instability and meibomian gland dysfunction. Methods: Subjects were enrolled in one of three groups: those who rarely wear makeup (No-M), those who wear it frequently but only outside the eyelid margin (Min-M), and those who wear it frequently and directly on the eyelid margin (W-M). Subjects were assessed for dry eye signs and symptoms by a masked examiner. Lipid layer thickness (LLT), tear meniscus height, meibomian gland excreta grade, number of glands secreting, corneal and conjunctival staining and tear breakup time were assessed. Results: 10 No-M, 18 Min-M, and 21 W-M subjects completed the study. Average fluorescein breakup time was 4.6 s in each group (p = 0.839, 1-way ANOVA). There were higher scores (worse findings) in the marginal eyeliner sample for symptoms (modified Schein, OSDI, SPEED), Oxford and total NEI staining and lower lid meibomian secretions. The W-M group demonstrated a statistically significant increase in the meibomian gland excreta grade (a worsening) compared to the No-M group (mean grades 1.2 and 0.55 respectively; Tukey test, adjusted p < 0.05, 95% CI 0.055–1.187). LLT, tear breakup time, eyelid marginal signs, and meibomian gland dropout had no differences among groups. Conclusions: Eyeliner wear both outside and on the eyelid margin demonstrated increased ocular staining and decreased gland excretion quality, compared to non-makeup users. The meibomian gland excreta decrement may lead to worsening meibomian gland function and potentially glandular atrophy over time.