If you’re concerned about eye liner lasting all day (or night), make sure your eyes are oil-free before application. After using an oil-free cleanser, apply long-wear, waterproof eyeliner for a look that will last. If you’re concerned about eye liner lasting all day (or night), make sure your eyes are oil-free before application. After using an oil-free cleanser, apply long-wear, waterproof eyeliner for a look that will last. Note: The prices above reflect the retailers' listed price at the time of publication. There are so many eyeliners on the market and we are on the prowl for the longest lasting eyeliner pen on the market. We want our eyeliner to stay black, to resist smudging, and to resist skipping. This last point is especially important for women like me who are older than 30 and noticed more tips here more folds on my eyelids. Although I can "pull my eyelids" back to make it smooth, doing so will stretch the delicate skin around the eye, causing it to droop and fold even more!