I don't know if this is helpful because I tend to be a little anal and over organized in some areas of my life
I put all my clothes into a spreadsheet with my tops in a column and my essentials (jeans, cardigans, jackets, skirts, vests, etc.) across the top in rows. I put an "X" in the box where two items meet (eg. patterned shirt with a cardigan and jeans or skirt top with a skirt). I try to get at least 3 outfit combinations out of each shirt, I strive for 4 - 5.
I know this sounds involved but it lets me see immediately where I can pick up a few items to make more outfit options or where I've duplicated looks. It also helps me remember what other outfit options I have for a particular top when I feel like I'm wearing the same thing over and over.
I should add the disclaimer that I was an accountant in my working life