Figuring out how to match patterns can be one of the most difficult challenges when you’re first learning how to dress well. The topic is only made more confusing with the number of convoluted tutorials found online or in books. Some kind of striped tie goes with some kind of checked shirt, but if you have a paisley, then you need this other thing. As though anyone is going to memorize these combinations or break out their tutorials when dressing.
You can match patterns successfully if you just follow a simple principle: things are always easier to pull off when they look distinct from each other. Think about how colors are combined – you want things to harmonize, but also look distinct. A dark-navy sport coat is easier to pull off when it’s matched with trousers that are in a distinctly different color (mid-grey or light-tan, to give examples). If your trousers are too close in shade and color to your jacket, you run the risk of looking like you tried to find matching pants, but failed.
Patterns are similar: you want them to look distinct. Thus, when wearing multiple patterns, vary them by scale. To match a striped shirt and striped tie, for example, make sure the spacing and thickness of the stripes vary. A block striped tie can be matched with a pencil striped shirt. You can also wear a checked tie with a checked shirt so long as the scale of the patterns aren’t too closely matched. Otherwise, you run the risk of creating a kind of dizzying 3D effect.
This variation by scale is more important than the often said rule of varying patterns by type, incidentally. A paisley patterned tie that’s too close in scale to a box checked shirt (such as a gingham) still won’t work, even if the pattern is distinct. You’d do better by choosing a tie with a much bigger pattern, again with the goal of making things look as distinct as possible.
Of course, style isn’t formulaic and in the end, you ought to dress according to your eye. It helps to know the principles, however, so you have an idea of what usually makes for a successful execution. That is: vary the scale.