Never. I have latex foam pillows that are a solid block, so there is nothing to fluff. It took me a while to get used to how firm they are, but I absolutely love them now.

I use a memory foam pillow. There is nothing to fluff.

have you tried buckwheat hull pillows? they're pretty firm and stay firm in my experience, and you can always take out or add more hulls for a more or less firm pillow - might be helpful?

I sorta struggle with this because I like to sleep on my back, but I like to get sleepy on my side first, and so my pillow needs to be thinner for back sleeping, but when I'm on my side I need more neck support - so I sleep with a little extra pillow or something like a shirt, robe, etc. that I can fit under my neck on just that part of the pillow (also helpful for throwing over my face / eyes so I can sleep in when it's light in the morning).

Wife and I have been using our Sleep Number pillows running on 6 years now. Good memory foam, doesn't need fluffing

I'm a stomach sleeper, so I prefer my pillow to be worn in and flatter.

Are you letting the sun “bake” your pillows? Lay them in front of a window or slider that gets good sun to bake them weekly, see if that helps with the fluffing.

Also i use those square pillows.

Pillow cube is one manufacturer.

With that said i find i have to replace my pillows annually.

i have to cram it all in the pillowcase and then fold the leftover pillowcase (I have a big pillowcase and normal sized pillow) under the pillow. i usually have to redo it once or twice bc I toss and turn a lot.

I fluff mine every night, it’s part of the bedtime routine. Am I not supposed to be doing that? I like my pillows squishy, down, and always sleep with two. I usually sleep with flannel except like three months in summer when I switch to linen.

I used to sleep on my side but I tend to fall asleep better on my back now. With a squishy pillow it curves up around my head and supports it to either side.

Every night, knead it like my cat taught me.

I have a feather pillow from Ikea that is a few years old at this point and it still fluffs up just as good as the day I got it. I wash it once or twice a year during the warmer months in the washing machine on a gentle cycle with a wool detergent and let it dry outside in the sun while regularly fluffing it and turning it around so it dries evenly and thoroughly.

While I don't like how feathers are harvested I also don't like how pillows with polyester filling get lumpy after a while and need to be replaced or repurposed because they stop providing adequate neck support. I'm crafty and have used pillow fillings for sewing projects and stuff like that, but already one pillow is enough filling for lots of projects and I can't craft enough to repurpose all so inevitably a lot would still end up in the dump.

All the while my parents still have some feather pillows from when I was a child that are still perfectly fluffy. So as log as I take good care of them, they will hopefully last me decades.

I bought an Ikea firm pillow over a decade ago and it's still just as good as when I first got it. I've been meaning to replace it but they don't make them anymore.

Check out the natural latex/wool pillows from Obasan. Love ours. They are quite heavy/firm..

https://obasan.ca/collections/pillows

We also have their wool duvet and love it, and prefer it much more than down.