Eye cosmetics are frequently applied among female populations of all age groups around the world. However, the migration of cosmetic products across the eyelid margin has been reported, and this is thought to exacerbate tear film instability and symptoms of dry eye. Furthermore, numerous adverse effects and complications have also been reported with eye cosmetic wear, and the associated inflammatory responses may potentially increase the propensity toward ocular surface disease development. Prospective studies have demonstrated that eyeliner application at the inner eyelash line is associated with higher levels of tear film contamination and ocular discomfort than application at the outer periocular skin. A recent randomized trial also highlighted the potential for eye cosmetic wear to compromise the efficacy of lipid-based dry eye supplements. This review outlines the current evidence base and understanding regarding the periocular migration of eye cosmetic products, the effects of cosmetic product contamination on tear film function, and the use of dry eye treatments in eye cosmetic wearers.