With older siblings, he is bound to be getting lots of hand me downs. I would get him something that is his alone, and something his siblings won’t automatically take over as theirs. Personalization or monogramming is the way to go to literally have his name on it.
Love the idea of one of those personalized beanbags or anywhere chairs. You could also have his name put on a backpack or lunchbox if he wants to be like older siblings, on a big beach towel or beach bag to bring to the pool or after playing in the sprinkler, or on a toy bin.
Otherwise, go practical: my toddler was thrilled to get a rain jacket, rain boots, and a tiny umbrella. You could do similar with winter gear. Replenishing heavily used things like crayons, paint, craft supplies, sticker books are also an easy spin.