I commute 5 days a week. Only time I don't commute is on days when it is pouring rain. One thing I hate most is that feeling of bulkness from all those clothing. I like thermal shirts such as Patagonia and an extra thermal over that during the winter morning. Then I just use a Rei Novara bicycling jacket over that to break the wind. If it is windy, I will also wear a green construction like safety vest with reflective strip over that.

As for the pants, I'm a big fan of 5.11 tactical pants. They are constructed on the heavier side which last longer than most pants, especially when the chain ring gear teeth snag on the pants whenever I have to carry my bike up the Bart stair. The heavier material they use for those pants also keeps the chill away. They have pockets everwhere to carry my smaller item. Along with that, some 5.11 sock are better than most regular sock. You can buys these at places that sell law enforcement store. Those store also carry a good line of gloves for security personel who has to work outdoor.