Wearing house socks with ankle boots are not recommended. However, you can choose to wear them this way if you please. With ankle boots, the entire footwear is covered, so wearing regular socks is the best choice since they won’t make you feel stuffy. You may wish to include woollen or any other thick house socks in this equation. In such situations, make sure you wear socks and boots in chilly weather so you don’t end up feeling uncomfortable.