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Combination sleepers have the hardest pillow problem. Side sleeping wants height to fill the shoulder gap; back sleeping wants much less, or your chin gets pushed toward your chest. A pillow set for one position punishes the other.
Two things solve it: an adjustable pillow you set to the lower end of your side-sleeper range, so it compresses acceptably on your back, or a medium pillow designed to squash down when you roll over. These are the picks that handle the switch without you reaching down to fold the pillow at 3 a.m.
Roll from side to back and most pillows betray you: what's right for your side is a cliff for your back. Casper's answer is a pillow-in-a-pillow (a supportive inner core inside a softer outer) that gives a medium, even feel which holds up on your side but squashes down enough that your back doesn't get craned forward.
Start here if you don't want to think too hard. You unzip the cover, pull a handful of shredded foam out until your head stops tilting up, and your neck sits level with your spine. That one feature solves the thing that wrecks side sleeping: a pillow that's the wrong height for your shoulder.
It does the Coop's trick for less money. Same idea, a zip, a bag of shredded foam you add or remove, a bamboo-blend cover, at a price that undercuts the name brand by a useful margin. Owners who cross-shopped the two tend to say the DreamyBlue feels a shade softer out of the bag.
The hotel-pillow brand's adjustable shredded-foam version. Two pillows, add/remove fill, cooling cover; a sensible step up from a plain soft 2-pack if you want to tune loft.
Two hundred dollars for a pillow sounds absurd until you've spent two years buying cheaper ones that didn't work. The Honeydew is a fully adjustable, made-in-USA pillow filled with a gel-infused shredded foam that stays plush without collapsing, and it's the one on this list that reviewers reach for the word 'cloud' to describe.