I was going through documents and pictures and whatnot and happened across this little diagram I had found a few years ago. I wish I could give proper credit, but I’m not sure who the original creator of this chart is.
How it works:
It’s pretty basic. Look at the pants at the top and then go straight down and this chart attempts to tell you what goes with them. Most of these seem obvious, but others are often overlooked. For example, for those just getting started, you may not be fully aware of the difference between a “Dress Shirt” and an “Oxford Cloth Button Down”. FYI: OCBD = Oxford Cloth Button Down. As a side note: The Oxford Cloth Button Down shirt is one where the collar points can button to the shirt (and should, unless you’re emulating a certain Italian race car driver). These are also known as the Original Polo Shirt as they were introduced to the United States in 1896 by Brooks Brothers after seeing English polo players wearing them.
I also wish there were more shoe options on the list, but if you notice you can readily see what two shoes you should look to invest a few dollars in. Definitely get a pair of high quality loafers and brown brogues. Allen Edmonds makes both of these in many styles. I like the McAllisters and the Waldens.