The pattern has covered board games for millennia — chess, checkers — and shows up in medieval church flooring (Cosmatesque work) and the heraldic charge "checky." It resurfaced in the late 20th century as the visual identity of skate culture (Vans) and the Jamaican-rooted ska/2 Tone music scene.
The structure is just alternating a square's colour, but that simplicity gets reused elsewhere — the grey-and-white checkerboard image editors use to represent an alpha channel (transparency) is the same pattern doing different work: since "no colour here" can't be drawn as a colour, the checker itself became the agreed-upon symbol for "nothing's there."
In CSS, two 45° linear-gradient layers cut at the 25%/75% marks, offset by exactly half a tile from each other, are all it takes. It helps to see houndstooth as this pattern with two more diagonal layers stacked on top.
When to use
Use for racing/skate moods, transparency-indicator UI, and flooring mockups. Smaller tiles read as flat grey from a distance.