Nike Free TR Fit Winter Women's Training Shoes

Taking inspiration from the brand's iconic sandals, the Originality design by Dr. Scholl's gets a boost from a sassy faux-wood platform.

Leather linings are breathable for allover comfort

Circa by Joan & David's Zanobia dress booties pack a one-two leather and suede punch that's utterly adorable when you mix them in with your cold-weather looks.

Refined height is but a step away. Truth or Dare by Madonna's Edwina riding boots feature buckled straps around the outside of the shaft that are topped with shiny metallic details.