Santa brought me some Shimano winter boots (though I was the elf who went to the shop!)
So they have a neoprene ankle cuff and are gore-tex, so how do people wear them?

Surely if you have leggings that go into the boot, water will track down the leggings inside the shoe, same goes for wooly socks that might peak above the cuff. So does it really matter or have people gone for a legging that stops at the ankle and keep socks buried?

All experiences welcome

Leggings over the top of the cuff.

put my shoes over the longs on my spec boots; never fill up with water.

Welcome to the world of waterproof footwear (both shoes & socks), and the realisation that water fills them from the top. Gaiters get recommended quite often on here, i’ve settled on long Sealskins inside mine limiting how long the trickle-down takes.

Leggings over the cuff means you cant use a legging with a stirrup or it hangs off the back/ front

So does it really matter

no

I run my leggings inside the cuff, but I have skinny legs otherwise I get a big gap round the top.