Originally from Scottland, it came about the same time as plaids. It is a classic print in men and women's wear yet old, very old. The tricky part is how to wear it without looking like one of your old literature professor.
The key to successfully wearing houndstooth print is picking the print itself and let its colors dictates other colors of your outfit. When wearing it, pick one item in the entire outfit to use houndstooth print or weave. To make your outfit more modern and up to date don't wear houndstooth jacket and pants together.
Unlike plaid or tartan, houndstooth is not as flexible in terms of mix or match. You can't mix houndstooth with other houndstooth, it's just gonna look crazy. You can try mixing it with plain tartan print but the color of the tartan cannot dominates the houndstooth.
It can work really well if other pieces of your outfits are plain colors that similar to colors domintates from your houndstooth piece. To use other patterns in your outfit with houndstooth, the pattern needs to be smaller than the houndstooth print itself.
Today's trend, there are many types of colors and sizes of houndstooth prints or weaves beside brown or black and white. Accessories also comes in houndstooth print. In my opinion the grey and black houndstooth tends to be the most modern looking one. Here are some examples on how to use this print well.