Andrew,
It took me a long time to find and dial in what works for me in those conditions, which fall in what I consider the most challenging temp range (wet and cold). Get it wrong, and if you stop (intentionally or for a flat) while still in the elements, hypothermia can set in fast. Now that I have it dialed in, it's incredibly satisfying to hang out on an autumn rainy day in an aspen glen I rode to and be warm and toasty the whole time vs "can't stop, gotta stay warm!" Grin.
Options to try and learn:
- Add a warmer hat. The 2-ply boiled wool is perfect for those conditions.
- Make sure your shoes/boots are upsized for thicker socks. Diminished circulation from constriction is not fun. Generally one size up will cover it.
- Boiled wool with sandals. I tested this and it works well for me down to about 25˚F. That's with the 3+ply over the knee socks. Just let 'um get wet and ride.
- quality thin, supple leather, upsized to accommodate the sock, such as the Ra II mentioned earlier.
- A duck boot/shoe, like from LL Bean. Unlined, so you can change socks when they take a while to dry.
- A gator to just under your knee to keep the splash out. I use a double ventile gator and it's fantastic.
With abandon,
Patrick