Follow Me

5 Pairs of Winter Boots & How to Wear Them

how to wear winter boots: snow boots outfit

Boots: Slimpack II Waterproof Boot, more colors here | Top: Striped Tee, also love this striped turtleneck | Jeans: Maternity Jeans | Socks: Cozy Winter Socks, more colors here

In November, my footwear choice is almost exclusively boots. Why? Umm, well, I love them! But, really they’re just so practical for this time of year. There’s literally a pair for every occasion! I’m always cold, and as long as my feet and hands are warm, then the sub-zero temperatures are a little more bearable.

Before I moved to Chicago, I think I had one pair of boots in my closet. Now, they make up the majority of my winter footwear—and when I say majority, I mean the vast majority. Like 95% of my fall and winter footwear is boots, anyone else? Depending on the weather and the occasion, I rotate between these five winter boot styles throughout the cold months.

casual snow boot outft
cute winter snow boots

casual fall outfit for moms

Fashionable Winter Boots to Have in your Closet


booties outfit

First and foremost, every gal’s closet needs at least one pair of versatile booties. Without a doubt, I have more pairs of booties than any other boots because I wear them so often. Skinny jeans or mom jeans (still love this mom jeans outfit) are a staple for me in the winter and booties look really cute with both of them. Booties with heels will elongate your legs and give you height—duh—and can also look dressier. For more casual outfits or everyday wear, a comfortable pair of flat booties in a neutral color will be your best friend. I picked up a pair from Dolce Vita last year and I was even surprised by often I wore them.

Best Winter Booties

booties shoes

I end up wearing my booties with jeans most of the time, but they look equally as cute with a skirt or dress! Unfortunately, it’s usually too cold to pull of this combination in the middle of a Chicago winter! I love this perforated pair and this pair of Chelsea boots—both are under $100!

Winter Snow Boots

winter snow boots

Okay, so if you live in Texas, Arizona or near the beach in California, you may never have a real reason to buy snow boots or waterproof winter boots (and I’m a little jealous), but for those of you who do live in climates that get cold, or if you’re visiting somewhere cold and snowy, you need a pair of these. I bought a pair of Sorel boots as soon as I moved to Chicago and have bought several more over the years. I love this tan color and finally bought them this year. They won’t set you back too much either—the pair I’m wearing here is under $150!

I used to think of these as pretty utilitarian, but there are some seriously cute winter snow boots! And, if snow isn’t your problem, they’re ideal for all types of inclement weather—think snow, sleet, rain or even chilly mornings!

sorel boots

These are completely waterproof and also warm. I recommend ordering a half size up in Sorel boots as they run a bit small, plus you’ll most likely want to wear a cozy sock to keep your toes extra warm! Another thing I love about these is that you can come up with some really cute casual snow boot outfits simply by switching up your sock and sweater combo!

Over the Knee Boots

flat over the knee boots outfit with skirt
over the knee boots outfit with a check scarf

Let’s forget sleet and snow for a bit and talk about the next pair of winter boots that I think is totally necessary—over the knee boots. Several years ago, I splurged on these flat over the knee boots from Stuart Weitzman and I’m not lying when I say it was one of the best purchases ever. No, they are not cheap—at all. But, they’re well made and look just as good as the day I bought them over three years ago. They also keep your legs really warm!

They’re sort of like a pair of pants since they go over your knee and depending on how long your legs are, they might go higher. When you wear them with jeans, it’s a double layer! If those aren’t in your budget, and I totally understand why, this pair and this pair are also super cute and look super similar to the Lowlands! Since they’re flat, I end up wearing them with casual outfits as well as with dresses and skirts for an elegant winter look.

Over the Knee Boots

I also love a good pair of heeled over the knee boots. This slouchy pair gets just as much use as my black pair. Again, these look really cute with dresses, skirts and jeans, but have a more casual, boho vibe that I love! This rich gold-brown color is my favorite!

Rain Boots

hunter boots outfit
I won’t lie, it took me a long time to get on the rain boot bandwagon, but I’m so glad I did. They’re one of those pairs of boots that you don’t really think about until it’s pouring down rain and you realize your sneakers aren’t going to cut it. Something I didn’t consider, was how versatile Hunter boots really are. They’re not just for rain! They work well in snowy weather (though you’ll need some thick socks) and are great for any weekend trips to the apple orchard, Christmas tree farm or any outdoor activity that might get messy. If they get dirty, you just hose them off!

Waterproof Boots

Now that I have a black pair, I really want more, haha! I love this army green pair, this glossy red and this short pair! These boots are pretty casual, so I stick with jeans and a sweater or a plaid button down shirt for everyday wear, though I’ve seen them styled with casual dresses like this which also look super cute.

Tall Boots

tall fall boot and a stripe dress outfit
Last, but not least, tall boots are a classic pair that’s going to be around forever. When I lived in Texas, this was the only type of boot I had! Actually, pretty much every Texan gal I knew had fall boots similar to these! Whether you like them flat or heeled, you’ll get a ton of use out of these. They look great with leggings or paired with a short skirt and fitted turtleneck.

Tall Boots

I prefer a chunky heel on these simply because they’re easier to walk in than super tall heels—who agrees?!

What’s your fall and winter footwear of choice? Do you have a specific type of boots that you like best?

Thanks to Nordstrom, a brand I love and trust, for sponsoring this post! Partnerships like this help make The Fox & She possible!

BTW, a simple and neutral fall outfit, and the perfect fall outfit.