MX-21 Black and Gold Wireless Headphones $29.99 Sleeping in headphones is a thickness problem before it is an audio one. A headband or eye-mask design keeps the speakers flat against the head so a pillow does not press hardware into the ear, which is the failure that wakes side sleepers.
Fabric that washes and a profile that stays under a cheek are what these listings describe. Sound quality is not what this shape competes on.