My 19 month old likes to lie on pillows and cushions so I tried adding a pillow to his cot to see what he thought and he hated it! I'll just wait till he's 2 or longer now.
As for pillows, you can get little ones that fit the cot pillow cases (I got a bunch in cot sheet sets).
We put a flatish one on DDs bed when she went to her own bed (around 18 months) but she still doesn't really use it when she sleeps, only when she is reading in bed.
DS1 started sleeping with a pillow around the age of 2.
DS2 on the other hand (who will be 3 in December) detests a pillow and refuses to sleep with one.
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