Shoes for winter if not walking

My kiddo is 7m and whilst he's doing amazing I don't think he'll be walking come October/ November. So I'm curious how i should be dressing him footwear wise.

I did buy some shoes when he was a couple months but they seemed uncomfortable and so I never bothered using them. I've just started putting socks on him more often as it's breezy (which often get kicked off and this is probably my fault) but as we get into those colder months I'm wondering what's appropriate? I bought some tights for under jeans/ leggings, so is it just thick socks over them? Am I completely overthinking this?

Also these converse/ vans are they a terrible idea for babies? I love them but don't want to hurt his feet.