Just learned that one of our salesguys' wife irons colored dots into the labels of his shirts and pants so that he knows what matches what.
Don't know whether to be impressed or disturbed.
When I was single and teaching, and had to match ties to shirts, I got help from coworker friends - labelled each shirt with a letter, and each tie with a number, and then they put together a list, so I could go "Shirt A can be worn with Tie 1, 3, 4, 5, and 8."
[I have color vision deficiencies]
I was going to ask what wild colors he had that things could clash so bad that he needed this system, but this gives a good example.
Most of my wardrobe is tame enough that if I avoid the brown slacks with a few specific shirts the rest is pretty interchangeable.
I had a boss who always wore black pants and shirts because he didn't want to figure out what matched what. He did eventually work a few solid color shirts into his outfits but always with black pants.
The instructor who taught the Personal Investment Strategies course at my undergrad (he had started and sold a mutual fund and was very rich) wore nothing but black so never had to spend time thinking about what to wear. One day took off a black sweater and a black tshirt was underneath.
As someone who spent years having his sister roast him for not knowing what matches what, to the point where I'm convinced nothing actually matches, I would welcome this.
I took the California Contractor course from a guy who always matched. He showed up one day in a complete burgundy suit with matching tie and a pink shirt.