Bob Hall's Ride-in-the-Rain Advice

Motivation

Riding your bike in the winter sucks. It's cold, wet, and visibility (both yours and that of drivers) goes way down. However, the extent to which Seattle is an awful place to ride in the winter is greatly exaggerated, shitty as it may be. We live in a marine temperate climate, so the temperature is regulated in a huge way. For all the people who say Seattle weather is horrible for biking, my challenge to them is this: Name me the city where the weather is great for biking all year. Coastal Southern California comes to mind (emphasis on the "coastal"). Besides that, most other cities have pretty horrible weather for a large part of the year: Chicago, New York, Minneapolis, Phoenix (summers), Houston, Boston, etc.
The point is this: Seattle has relatively mild winters, but it is dark and wet and that's no fun either. I keep promising to move to Santa Barbara and someday I will. But in the mean time, here's how I get by.
By the way, I approach this topic with a real specific bent. All the gear I use is chosen with these 2 things in mind:
1) Looks good. Imagine the typical commuter: neon green jacket, spandex, etc. I don't want to look like that.
2) Price. One of my main reasons for cycling is to be frugal. Frugal doesn't mean cheap. It means knowing when to plunk down the $200 on the good version, but also when to skate by with what works.

Fenders

Buy some. This bit of advice is not original, and there are plenty of places to read why they are the best thing ever.

Clothing

It's an article of faith in Seattle that you're supposed to deplore cotton and love wool. This is reasonable enough, although it tends to get fetishized a bit. Keep an eye out and you'll see dudes clad head-to-toe in wool, panties included. Having said that, go buy a used Pendleton shirt somewhere and some Smartwool socks. Both of these items will serve you well.
You'll see a lot of bicycle-specific wool pants for about $120. They're nice, but I consider them prohibitively expensive. My choice is something I call "Old Man Cowboy Pants." They're polyester with a splash of spandex mixed in.

They cost about $34 and repel rain equally as well as wool. I buy mine from Shepler's Bonus points if you hem them into shorts. This combo, with black polypro long underwear is my battle uniform.

Shoe dryer!

This is the number one piece of equipment that I don't hear people talk about much but I find indispensable. It'll set you back a whole $30. You can buy one on Amazon It's easy: put your wet shoes on when you come home at night and then find yourself delighted in the morning when they are bone dry. My girlfriend can testify that this GREATLY reduces foot odor.

Gloves

When it gets really cold and shitty in December/January, I've gained a lot of pleasure by donning these fine gloves.

They're not waterproof, but they are warm. I buy mine at H&M for $6. Buy 3 pairs, and rotate them daily when they get wet. Keeping an extra pair in your bag for your poor friend wearing "cycling gloves" gets you extra credit.

On Brook's Saddles

The Brooks is extremely popular, but you'll hear a lot of ignorance about how leather can't hold up in wet conditions. Go tell that to loggers. That's why I use a proper beeswax-based boot treatment sold by White's Boots in Spokane, WA. Don't use those silly little plastic bags to cover your saddle. Use this: White's Boots Preservative Brooks will sell you a tin of leather preservative, but for a lot more money.

Radar

Some advice from Cliff Mass: Use our new fancy radar to see when the rain is coming!

You can use this tool to make your own short-term weather forecasts. For example, sometimes you can see that it's raining now but it's going to blow away with clear skies behind it. Sometimes it's worth it to wait at home for 20 minutes knowing that the rain will clear up soon. Link here