Q How can I get my eyeliner to stop giving me raccoon eyes? —Ashley
A: Dear Ashley, The descent of liner/mascara/eyeshadow is as inevitable as it is dispiriting. If, like me, you like to moisturize all day and wear any sort of eye makeup at all, you are going to have that awful moment when the insanely cute man peers searchingly into your eyes and says, “What’s that on your face?”
You can have fewer of those moments if you wear all-waterproof. I say fewer because waterproof does not mean constant-application-of-oils-and-creams-proof. That said, the fat 24/7 eyeliner crayon from Urban Decay is the greatest. It is soft and the black is super-black, so you can just ink a little along your outer-upper lashline, pre-mascara. So you’ll need much less mascara—the worst offender in the raccoon-eye department. You can also circle the pencil wildly around your eyes and do the easiest smoky eye ever. You have a minute or so to blend before the formula settles into relative permanence; powder eyeshadow over the liner, in the same color, makes it stay in place longer.
Concealer and eye cream are the natural enemies of eye makeup of all sorts, but in the end, I always choose a better-looking undereye over the possibility of raccoon eyes. If you disagree, congratulations, as you must have been born with less-noticeable undereye circles, and the world is your oyster!
Erwin Blumenfeld/Condé Nast Archive