Originally Posted by mihlbach

At some point you have to stop planning and start riding. Years ago, I stated commuting with a bike and a backpack filled with work essentials and nothing more...there was no planning. Over time you'll discover what is worth bringing with you and what is dead weight.

Your first winter will be a fun challenge as you discover, via trial and error, what kind of clothing and how much clothing to wear. In the winter the first thing I do every morning is evaluate the day's forecast, then spend the next 5-7 minutes in the shower pondering what combination of clothes will work best for the day.