A longer skirt looks great with a knee high boot but you can also always wear a pair of jeans with them. I know that kind of defeats the purpose of the higher boot BUT you can still wear them and the pointed toe looks great with a boot cut jean! You should look at some of the western wear here http://www.FortWestern.com/, they shoot a lot of their product with pointed boots...you can find some great wear on their site. =)