I rarely seem to plan my outfits anymore.
Texas weather is very bi-polar so waiting until the day of is usually my best bet. Shoes are usually the first thing I think about when planning an outfit. I'm sure that sounds a little crazy, but here's my logic...
Picking my shoes first keeps me from wasting time choosing an outfit that requires shoes that may not be ideal for that day.
Next, I decide what mood I'm in...dress/skirt, jeans, or trousers. After that I choose my layering pieces (cardigan, scarf, blazer, etc.)
Honestly this process usually takes me about 10 mins. I just use my imagination and go. And once you have your closet memorized outfits naturally pop up in your head. It also helps to think of past outfits you've made and find ways mix and match that outfit with current items in your closet.