When you're done looking over the list, you may want to check out readers' feedback on which brands make the warmest winter boots or share your own thoughts on the matter.
The North Face 'Snowtropolis' - Tall and Cool
Easily one of my favorite styles on this list, the 'Snowtropolis Tall' from The North Face features loads of practical features, including uppers that combine waterproof leather and suede; PrimaLoft insulation; and full side zippers.
But the let's get real, while all of those things are great, these boots look absolutely fantastic. They're different, they're casual, they're cool. And, they're screaming to be paired with your favorite jeans or leggings. I'd even wear them with a pair of tights and a cute, casual skirt for a kind of intentionally sloppy look that works so perfectly in winter.
The fact that they'd also be effective as winter boots is really just icing on the cake.
Stylish Boots from Sorel - "Joan of Arctic Wedge"
Though these boots share their name with the enormously popular, faux-fur topped 'Joan of Arctic,' looks-wise, there aren't a lot of similarities.
The originals are flats and obviously winter boots, but these stylish mid-calf boots could be worn as well indoors as they could out -- probably better since you may not want to risk wearing 3" heels on slippery streets.
But where ever you choose to wear them, these wedge-heeled boots would look great with jeans, leggings, or tights and casual skirts. Available in gray or brown, they also play perfectly into this season's short and casual boot trends.
Timberland Earthkeepers 'Mount Hope' - Mid-Calf Casual Boots
Ideal for those cold days when you still want a healthy dose of casual style! These tall winter boots from Timberland have a slew of features that will protect you from the harsh elements, like PrimaLoft insulation and waterproof membranes.
Style-wise, they're no slouches either, featuring lace-up fronts; faux fur linings; and an overall sporty design. Offered in brown, gray, black, and winter white, these boots ring up at just under $150.
Kamik 'New York' - Cute Lace-Up Boots
There's no reason you can't be cute and warm this winter, and these Kamik boots accomplish both.
As well as being 100% adorable, these 'New York' winter boots have faux fur trim; foam insulation; fleece linings; and quilted, waterproof nylon uppers. Available in gray, black or red, these mid-calf boots have lace-up fronts, and a great casual look.
For other sweet styles, be sure to check out my top picks in Cute Winter Boots and Snow Boots for women.
Tecnica 'Moon Boots Vinyl' - Classic Winter Boots get an Update
Most of you are probably familiar with Tecnica's iconic "Moon Boot," but you may not be aware of the fact that there are actually several variations on this classic winter boot. There are tartan and rainbow versions, there's a shorter style, one called the "puddle jumper," and even a suede version. But one of my favorites is this glossy "Vinyl" Moon Boot.
Available in lots of shiny colors, including black, red, white, and azure blue, these boots feature 15" tall shafts made from vinyl to keep your feet dry; and soft, fabric linings to keep them dry.