Here, sleep specialists name their top pillow picks for side sleepers and spill some tips on how to position them for your most comfortable night’s rest: She also emphasizes the importance of finding a pillow that’s just right for you and sticking to it. “Each person should have their own [pillow] set that has the correct sizes rather than bed partners sharing pillows night tonight.” Find a store that has a good return policy and try out several pillows to find one that gives you the best night’s sleep and the best head support for side sleeping.