Done a few of these and it’s tight but doable. Best trick is rolling everything and sticking to one pair of shoes. Packing cubes help but even a couple zip bags work fine.
As for a pillow stuffed with clothes… Ryanair usually counts anything in your hands as part of your one item. If it looks like a pillow you might get away with it, but if it looks like a bag full of stuff they’ll call it out. I’ve seen people use those compressible travel pillows and no one cared, but it’s always a gamble.
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