My Winter Boot Roundup

Now that we’re in the dead of winter, I thought I’d share my top picks for winter boots. I’m going to share the ones in my closet and how to wear them as well as share other favorites down below. Let me know if you have any questions about sizing or quality, etc.

Weather Boots

Tall Rain Boots

I love wearing my rain boots with high waisted jeans. The boots are a tad overwhelming on my short legs, so to help with elongate them, I wear high waisted jeans. I also wear these with black leggings

Shearling Boots

This is my first pair of boots like these and they’re so comfortable! I will wear these out and about when I’m running errands to walking the dogs. I like this style with the shaft folded down – it helps not overwhelm my legs. Since they’re quiet bulky, I will wear these with a monochromatic black look.

Hiking Boot

There’s so many cute hiking boots out right now. I initially wanted a pair of flat ones, but I realized I needed a little height, otherwise my legs look cut off. I found a pair of wedge hiking boots and I’m obsessed. Probably not the most practical, but they’re comfortable, easy to walk in, and keep me warm. Love this style paired with skinny jeans and leggings.

Hunter Tour Rain Boots 5

Koolabura Short Boots 5

See by Chloe Martinica shearling trimmed ankle boots 35

OTK Boots

OTK boots are great to stay warm, but also dress up a look. I love that the heeled option adds height, but the flat version is great for walking around. OTK boots are a great way to change things up in the winter when you feel like you’ve been wearing ankle booties forever. When choosing OTK boots, make sure you’re choosing a pair that are slimming along leg and not overly bulky.

Stuart Weitzman OTK Boots 4.5

Stuart Weitzman OTK Boots 4.5

Marc Fisher OTK Boots 5

Heeled Boots

I haven’t been into heeled booties until recently. I don’t know why I haven’t worn them in the past, lol. Now, I can’t get enough. Heeled booties can be tricky, thought. Unless you’re wearing sock booties, which I recommend wearing under your jeans (a wide leg or straight leg), I like my heeled booties to hit right at my ankle. This way you see as much of your leg as possible, otherwise you’re goin to cut off your legs. If you’re tall, this isn’t an issue. But, if you’re short like me, you want as much of your legs to show as possible (hense all the high-waisted jeans I’ve been wearing). You also want to stick to a heel height of 3.5″, that way they’re still comfortable enough to walk in.

Ash Booties 5 (sold out, similar)

Steve Madden Sock Booties 5

Flat Boots

Hands down, my favorite boot to wear in the winter. Comfortable, easy to wear, and pairs well with anything. I mentioned it on my Stories a couple weeks back, every mother needs to own a pair of black pointed ankle booties. They elevate your outfit instantly and they’re so comfortable. You can easily chase your kids around in them!

Marc Fisher Yale Booties 5

Marc Fisher Yale Booties 5

SHOP WINTER BOOTS