We report a series of 10 patients who underwent inferolaterally based V-Y advancement flaps for reconstruction of defects involving the lower eyelid and infraorbital cheek junction. Defects ranged from 1.7 to 2.9 cm in largest diameter, and patients ranged from 59 to 84 years of age. All patients had excellent functional and cosmetic outcomes without subsequent surgical or laser revision. There were no instances of flap necrosis, hematoma, or ectropion. Vertically oriented V-Y flaps are often underused in this setting largely due to the perceived increase risk of ectropion. We describe a modification of the flap with lateral orientation that both diminishes the downward tension vector, which threatens ectropion, and conceals incision scars within resting tension lines, providing superior functional and aesthetic outcomes. Our series demonstrates that a properly designed and well-executed inferiorly based V-Y advancement flap can be used as a safe reconstructive modality for defects involving the lid-cheek junction.