Originally Posted by Rowan

The water won't just come in from the bottom, it seeps up the sides of the shoe. And if you sweat a lot in your feet, it will be the same story as for waterproof jackets -- your shoes will get soaked anyway.

I've been through various iterations of booties. The neoprene ones are OK, but the ones I prefer at a more loose fitting waterproof fabric like that on a jacket.

Plus, they all wear out quite rapidly in the toe.

Why don't you got he whole hog and invest in a pair of waterproof shoes/boots. Shimano and others make them, and usually they are lined with a breathable fabric such as Gortex. That way you solve the issue, stay drier and certainly stay much warmer.

They aren't the coolest looking item in the peloton, but you can laugh at the misery of those with good fashion sense.