Given that it's only October, perhaps a post about cozy winter boots is a bit premature. But it's never too early to plan! Last year, I tried on the Timberland Earthkeepers Granby boot, and was pretty excited about it. It's a knee-high lace-up boot that I think would be great for walking around. I sometimes walk to work and envision these being good for the 30-minute walk each way when I wear skirts or skinny jeans/pants. Because of the laces, I was able to tighten them snugly around my 12-inch calf. I liked that added just enough bulk to the lower half of my leg to make my calves look nicely filled out. I also liked that they were a bit rugged, yet still feminine. They do run small, so order at least a half size up. I wear a 6 (sometimes a 6.5) and a size 7 fit best. The 6.5 was still way too snug because the inside is entirely lined with fleece.
They're currently at Endless
. I tried out Endless for the first time this year and liked it. The free 2-day shipping and returns were great. Plus, I had to call customer service for some help with my order and found the rep very helpful. The boots are also at Zappos (limited sizes) and Piperlime, and probably a bunch of other sites including Shoebuy and Planet Shoes, which offer free shipping and regular promotions. The comments sections on all of these sites might help with questions you have regarding fit and quality. For example, one person felt the boot was best suited for very slim calves because its natural thickness could make even average size calves seem overly bulky.
Update - I was able to try on a pair in black (pictured above) and they're not exactly how I remember them. I still think they're cute but the beige-colored fleece is much more drab/dull looking than it initially seemed. I also read some reviews that say the traction on these is bad on ice.
. I tried out Endless for the first time this year and liked it. The free 2-day shipping and returns were great. Plus, I had to call customer service for some help with my order and found the rep very helpful. The boots are also at Zappos (limited sizes) and Piperlime, and probably a bunch of other sites including Shoebuy and Planet Shoes, which offer free shipping and regular promotions. The comments sections on all of these sites might help with questions you have regarding fit and quality. For example, one person felt the boot was best suited for very slim calves because its natural thickness could make even average size calves seem overly bulky. 
Update - I was able to try on a pair in black (pictured above) and they're not exactly how I remember them. I still think they're cute but the beige-colored fleece is much more drab/dull looking than it initially seemed. I also read some reviews that say the traction on these is bad on ice.
