Commuting is complicated if you look at all the details involved and what it takes to solve them. But this is true of everything.

In real life, it's a slow refining process. If you do a dry run on the weekend, you know what you need to change immediately. Eventually, you'll know what to wear on each type of weather day, and you'll be placing everything in the right place in your home so you're ready to leave whenever you need to. You can take months to refine your gear and your process, and you can have a disaster-free commute every day from the first day.