I've been eying the Eliotte Toggle booties from 80%20. I love how warm and comfy they look, just perfect for winter! I like them in black pony hair, but I absolutely adore them in this geometric print. With the signature 80%20 hidden wedge, they would look hot with leggings. And in this print, these booties would be a great touch to a layered look.
These desert boot-inspired shoes are quite affordable. You can find them for $80-$115 depending on the color at endless.com and karmaloop.com. You can also find them at anthropologie.com, but they'll cost you $158 there.