Discoid lupus erythematosus (DLE) is the most common form of chronic cutaneous lupus erythematosus commonly seen in photoexposed regions. Eyelid involvement in DLE is relatively rare. We present three cases of DLE with eyelid involvement. It closely mimics many clinical conditions; hence, diagnosis is often late. When left untreated, it can lead to many complications. The aim of this case series is to emphasize that ophthalmologists and dermatologists are aware of the various presentations of DLE in eyelids to prevent any misdiagnosis.