Sky-high heels are not the only shoes that you can wear with dresses. Boots, specially cowboy boots, can also be worn with dresses, provided it is the right kind of dress. Wearing boots with jeans is chic and stylish. For a bohemian and casual look, there is nothing to beat the combination of rugged cowboy boots with floaty and feminine dresses. To carry this look with panache, you need to choose dresses that end above the knee.