I have tried bags over socks before, and I generally cut the tops off so they don't really show outside of my shoes.

FWIW the bags made ZERO difference for me.

[MENTION=175954]Tundra_Man[/MENTION], good thing you weren't riding a fixed gear! Can you imagine the injury?

OK, so if I put a bag over two socks and make sure it doesn't dangle, I should be OK. But it's not clear what works best with a bag, and as [MENTION=301784]PatrickGSR94[/MENTION] says, maybe nothing. I suppose I could experiment by doing different things with different feet.

I'm thinking that nothing is going to work for me short of some sort of chemical or electronic warmer unit. My super long toes just don't handle being in sub-freezing temps for nearly 90 minutes very well.

My commute might end up being that long this winter, too, so keep us posted. Last year, I was not open to these ideas, but this year I am. I'm in New York City, not the winteriest place, but it's extremely windy, and my route is right along the Hudson River which is over a mile wide and even windier than the rest of the city. Some of my rides last winter were brutal. My route is 13 miles each way.

By the way, there is a Winter Cycling section of bikeforums.

I have some PI toe covers in size XL that are VERY snug on my size 44 shoes. I don't think they'd go over a size 49 shoe. Mine are just the toe cover, and don't go around the heel at all.

Did you see my post regarding the Bontrager covers? Like I said, I have a 47 Giro and the XL (for 45-46 shoes) went on with some effort, but they make an XXL for size 47-48 shoes. I'm sure the XXL would fit easily onto my 47's. I keep meaning to buy these for winter:

RXL Waterproof Softshell MTB Shoe Cover - | Bontrager

They have some of the features you like in the giro, including a warm lining.

Bags over wool socks cut the wind a bit, giving me another 5-10 degrees.

Since I can't justify winter shoes ($350!!) for 5-10 days a year, I make do with ordinary, optimized-for-summer shoes. The Showers Pass covers I linked to earlier block the wind outside the shoe, and the wool then seems to work even better.

But of course, YMMV.