I really recommend the the Ariat brand for riding boots. They have a good variety of styles to choose from and the tall boots and 1/2 chaps come in many different widths and heights, the most choice available in sizes compared with other off the shelf brands. They are also made to last, very durable. I have had all of mine for ages, they clean up well too.
I have 4 pairs of paddock boots in lace up and zip up styles (I prefer the zip ups), 4 pairs of 1/2 chaps, 2 pairs of winter paddock boots (lace up and zip up), and 1 pair of tall boots with lacing all down the outside of the leg, I can't remember the name of them. I also have a pair of the "Terrain" style of sneakers. I have 1 pair of tall boots as well, the "Bromont", it is a field boot style that is waterproof.
You could go with a nice pair of paddock boots and a pair of leather 1/2 chaps, they look really nice together, almost like tall boots. I suppose if you want to compete in them as well, a pair of tall boots may be a better choice. Ariat International