Forget struggling with baby socks in winter: let them wear tights
Fiona's hack makes me remember back to my kids' baby days...was always trying to cover up that bit of exposed leg between the bottoms of their pants and the tops of their socks. This would have done the trick...
I read your hack about sockless baby feet - nice one! But I have another suggestion...put them in tights! Yes, baby boys can wear tights too, try white, navy, red, green, grey and stripey tights. The tights keep their legs warm in Winter and there is no danger of losing socks in the house, on the street or in the wash. Both my girls and my little boy are all in tights from now until April. They can be worn with trousers, joggers, dungarees. Even better, tuck in their shirts so they don't ride up under dungarees or coats.
Only thing: most tights lack the non-slip stuff on the soles, so if your house has hardwood floors, I'd put some slippers on the kid. I've also heard that puffy fabric paint (available at craft stores) adds grippiness, but I haven't tried it myself.
Related: Duct tape makes socks non-slip