Cowboy boots tend to be very decorative and festive and come in all colors of the rainbow plus some these days. They look great, although many people who wear them have probably never seen a horse never mind ride one daily or ever! Are these boots actually functional and did real cowboys wear such decorative boots?
First let us distinguish between boots for pleasure and work boots. Many people wear cowboy boots because they like them, because they look very good, and yes, because they can be very comfortable. Others wear them because, well, they are great for riding. These two uses are not mutually exclusive and many working boots are also very fashionable.
It was during the cattle drive era of 1866-1884 that cowboys started buying and wearing fancy boots, with cutout patterns, embroidery, and more. They were able to as their pay rose dramatically during these period. It is from this legacy that fancy and fashionable as well as functional boots arose.
If you're looking for a pair for pleasure, you probably want to choose a pair that goes well with several outfits. For men this may mean a basic brown or black pair with some decoration, although of course lots of options are available for men and women.
I know several women who own multiple pairs in different styles and colors and use them all too.
If you are looking for a pair for work, then durability and waterproof are probably at the top of your list.