Shirt dresses with ankle boots and even western-inspired ones are perfect all year round. Taller boots such as knee-height and over-the-knee boots make great Winter footwear choices.
You can choose matte black or patent leather ankle boots with a pointed toe and stiletto heel for a fancier look with a simple black or white shirt dress.
With the right style of shirt dress, thigh high boots can look great. I personally love wearing block heeled tan suede tall boots with a mid to long length shirt dress.