Despite taking countless red-eye flights over the past 20 years, I've never been able to crack the code on how to sleep on a plane . If I’m being totally honest, I’m pretty lousy at it: A bout of rough air will jolt me awake in a sheer panic, and fellow passengers' screens and the plane's overhead lights will keep me up for hours. By the time I’ve reached my destination, I’m usually exhausted and cranky, and rocking a killer headache. Truthfully, I was tired of being tired after a flight.

All of my jet-setting friends swear by wearing an eye mask on the plane, but finding one I actually liked proved to be a challenge. The cheap ones handed out by flight attendants are…well, cheap—and they're usually too tight around my head. Other sleep masks I've tried in the past would press down on my eyelids, which was incredibly uncomfortable (and felt like a stye waiting to happen).…