My answer to this would be it depends on what riding i'm doing and also what time of year it is.
If I'm touring, I take
altura goretex overshoes no matter what time of year it is. This is because I can't deal with wet feet while touring, and there's nothing worse than putting wet shoes on in the morning. I've also been known to wear waterproof socks and goretex overshoes, I hate wet feet so much! I also wear these on winter rides because they're so warm.
If I'm training and its june - sept, I'll wear some super-tight descente jobbies. Surprise surprise I also hate cold feet, and they get very cold. In the shoulder months (mar, april, may; oct nov) i've got some other altura ones which have reflective strips on and are a bit thicker...
If I'm mtbing I wear winter boots with waterproof socks, which works OK.
Yes I am anal about overshoes...