To turn all your essentials into wearables, try a pocket-addled travel jacket like this hoodie from SCOTTeVEST. The casual sweatshirt has 21 pockets to help you lighten your baggage load, and will comfortably fit bigger items like an iPad or a water bottle. It’s basically a carry-on bag you can wear.
My favorite wireless headphones, SleepPhones look like a soft headband but have wireless speakers inside that will allow you to sleep in any position on the plane. You’ll forget you’re even wearing them: I use them to turn on white noise that lulls me to sleep when I’m restless in a new place, and they can double as an eye mask.