I commute year round in Portland. In the winter, it rains all the time, and in spring and fall, it rains most of the time. It also gets chilly, with a typical winter commute in blowing rain at 35 F.

Jacket is an old Burley. Great jacket, I even have a spare tucked away. But Burley no longer makes apparel, so I'd buy the Showers Pass jackets which started out as copies of the Burley. The key is completely waterproof fabric (breathability is secondary), huge zippered underarm vents plus a wide back vent, and a rain-proof front zipper. Buy a larger size so that the jacket is loose enough for airflow and layering.

Rain pants are Castillo. These have held up for me, two years and counting. The legs are slim which prevents fabric from getting caught in the chainring. They don't vent, which is disappointing.

Booties are some cheap neoprene ones, the whole rear opens up w/ Velcro fastening, so they fit easily over my size 10.5 shoes. Neoprene is not fully waterproof, though, and water also gets in through the cleat slots in the bottom of the SPD shoe. Right now my shoes get a little wet during the worst days, while the rest of me stays dry. Next winter I will try some Showers Pass booties, which look more waterproof and have full soles. I will try to cut a tight-fitting hole around the cleat.

I mostly wear gloves to stay warm, because I am not bothered by wet hands. Last year I used some Castelli neoprene gloves which gave me damp but fairly warm hands. When it is particularly cold, I wear ski gloves.

A cycling cap under my helmet keeps my head dry enough. When it is cold, I may wear a thin balaclava too.

Dressed like this, I can stand in the shower and stay dry, other than some wetness in my shoes.