Floppy eyelid syndrome (FES) usually affects middle-aged obese men, presenting as a unilateral or bilateral chronic papillary conjunctivitis. The upper eyelid is lax, floppy, and easily everted. The laterality corresponds to the side the patient sleeps on. An association with obstructive sleep apnea (OSA) has been suggested. A personal series of 17 new cases is presented, and 79 previously reported cases are reviewed to give a detailed description of the syndrome. In addition to the classical presentation, patients may present with upper lid ptosis, lash ptosis or trichiasis, lower lid ectropion or rarely entropion, or corneal complications. Eight patients with FES were investigated for OSA. Twenty other patients with known OSA were examined for FES and other possibly associated ocular features. All eight patients referred for sleep studies were found to have OSA. One of the 20 patients with known OSA was found to have FES, and two had features of early asymptomatic FES. One patient with FES and OSA had normal tension glaucoma. Patients with FES should be considered for sleep studies because of the known morbidity of OSA. Simple screening of patients with OSA may detect FES and avoid late corneal complications that can compromise vision.