Vertebrobasilar insufficiency (VBI) after rotation or hyperextension of the neck during otherwise routine activities is uncommon "hairdresser syndrome" (HDS). We report three such cases presenting with neuro-ophthalmic complaints (Horner syndrome, ophthalmoplegia, and transient vision loss). A retrospective review was performed of the electronic health records of three patients seen in the neuro-ophthalmology clinic of Houston Methodist Hospital with acute neuro-ophthalmological signs after neck hyperextension. A literature review was also performed. While various ischemic signs of VBI have been previously documented, to our knowledge, these are the first cases in the English ophthalmic literature to describe the presenting neuro-ophthalmologic signs of HDS. Clinicians should consider the possibility of neck hyperextension as a potential mechanism and precipitating event for acute neuro-ophthalmic presentations of VBI. Patients with a history of occupational (e.g., carpenter), recreational (e.g., bow hunter), or cosmetic (hairdresser) neck hyperextension (i.e., possible HDS) should undergo structural and vascular neuroimaging of both the head and neck (e.g., CT/CTA or MRI/MRA) to look for evidence of posterior fossa ischemia and/or vertebrobasilar lesion (e.g., occlusion, dissection, FMD, and pseudoaneurysm).