This achievement just requires you to be "in the air" (any time your feet are not on a surface) for 60 minutes. This is cumulative over all worlds you enter, whether your own or a friend's. It counts time spent falling, jumping, flying, or grappled to a wall/ceiling while wearing wings or any flying accessory (even when you are stuck in cobwebs - thanks DottyRoxy69).
This does come naturally with regular gameplay. You only need 60 minutes total of air time while wearing wings.
FASTEST SOLUTION*** Spoiler - click to reveal ***Use any grappling hook and latch onto a ceiling or wall. Then just idle until the achievement pops. It is easiest to tell if you are "in the air" if you have the hoverboard equipped as an accessory because it shows up whenever you are airborne under your feet.
***Same as 360 version***