Winter Boots and Shoes

Shearling Lined Bean Boots / Brown Leather Ankle Boots / Black Suede Ankle Boots / Black Matte Short Hunter Rainboots / Joan of Arctic Waterproof Suede Snow Boots / Sorel Waterproof Ankle Boots / Hunter Shearling Snow Boots / Sorel Quilted Snow Boots / Black Over-The-Knee Suede Boots / Black Knee-High Boots / Black Knee-High Suede Blade Heel Boots / Brown Riding Boots / Brown Leather Knee High Boots

Here are a few of my favorite winter boots and shoes. From booties to snow boots to tall boots to rain boots, all of these styles are great winter wardrobe staples.

Shearling Lined Bean Boots: They’ve been a cold-weather staple in my wardrobe for years and have got me through some of the toughest Chicago winters. From my experience L.L.Bean’s warmest Bean Boot, and certainly the coziest, are the shearling lined ones. You get the best of both worlds with this pair, the classic Bean Boot look, and the added warmth. They truly keep your feet toasty even on the coldest winter days. The tumbled leather makes this pair SO much more comfortable and requires zero break-in time. Half sizes go down half a size, full sizes go down a full size.

Brown Leather Ankle Boots: You can never go wrong with classic leather ankle boots. The chunky heel on the booties allow me to walk for miles in the city.

Black Suede Ankle Boots: These are such a versatile pair of booties for winter. They look great styled with skirts or demi-boot jeans.

Black Matte Short Hunter Rainboots: If it’s not snowing this is my favorite pair of rainboots. Wear them with a pair of cozy socks and you’ll be good to go.

Joan of Arctic Waterproof Suede Snow Boots: When there’s a foot or more of snow, I like these snow boots. They’re incredibly warm and most importantly very waterproof.

Sorel Waterproof Sneaker Boots: My favorite Sorel sneaker boots are on sale! These sneaker winter boots are incredible. They’re waterproof, super comfortable, and warm. I wear them most of the time in the winter. Go up half a size.

Hunter Shearling Snow Boots: How cute are these shearling hunter snow boots?! (available here too)

Sorel Quilted Snow Boots: Another great pair of snow boots that will keep your feet warm and dry when there’s a lot of snow. The quilted leather makes these a little more stylish than your classic snow boot. (available here too)

Black Over-The-Knee Suede Boots: Black knee-high boots are such a versatile piece in my closet for winter. Wear them with skirtsdresses, or pants. These are under $70!

Black Knee-High Boots: These are under $25!

Black Knee-High Suede Blade Heel Boots: And these are 25% off with the code “WINTER”.

Brown Riding Boots: You NEED these super comfy riding boots! They’re under $120 and TTS.

Brown Leather Knee High Boots: Another one of my favorite pairs of riding boots. SO COMFY! Order a half size up so you can wear thicker socks. I love styling them with sweater dresses or skirts in the winter.