As winter rolls around, and snow starts piling up, make sure you have the proper boots to endure the elements. For my first winter in the snow, I thought I was going to survive by wearing just my waterproof hiking boots. Boy, was I wrong.. (I grew up in Florida. Don’t judge me 
)
Not only do my hiking boots look terrible for everyday wear, they also have zero insulation. Don’t make the same mistake I did, and scoop up any of these cute boots for your next winter. I compiled this list of all the cutest styles from my favorite, high-quality brands. You’ll be super stylish, and appreciate the fact that your socks aren’t soaked, and your toes aren’t turning into ice cubes with any of these winter boots.
But first, let’s make sure you’re buying the right boot for the type of winter you’ll be experiencing.
How to Pick a Winter Boot
A winter in South Dakota, where they get blizzards just about every two weeks is going to be entirely different than a winter in California, where it’s definitely cold, but you still want to look stylish for days out in the city. Consequently, the type of winter boots you buy will be highly dependent on the winter experience where you live.
Boots for Snowy Winters
For more intense winters, such as those in the Midwest, you may need multiple boots for different situations. I like to use a shorty or mid-height boot when there is slush or about an inch of snow out. On days where the snow is heavier, tall boots are more ideal.
Regardless, you’ll always want waterproof boots for use in snow or you risk the chance of snow and water seeping in. Remember: wet feet are cold feet!
You might also want to look for a boot with insulation if you find that a wool sock is not enough to keep your toes warm. For me, I think this usually happens when temperatures drop into the 30s (~0°C) and especially below 0 (-18°C).
Lastly, it’s good to consider the traction of a boot, as snow usually results in slipping on hidden ice. However, I have yet to find a boot that is 100% slip-resistant, so don’t be disappointed if you’re still falling on your a$$.
Don’t forget to consider sizing up if you’re planning on wearing wool socks or any other type of sock that will be bulkier. It is most helpful to read customer reviews to understand fit. Also, check the return policy to see how much returns will cost if you’re unsure how your boots will fit.
*I recommend buying durable socks from Darn Tough or Smartwool.
If you can only get one pair, I definitely prefer my midi boots over my tall boots, because they are just all around more wearable. I personally like boots that look similar to sneakers or combat boots, because I feel like they transition well from fall to winter. On the other hand, I feel a little ridiculous wearing my tall boots with the faux fur cuff when it is hardly even cold outside.
Boots for Mild Winters and Fall
For milder winters or during the fall season, where snow isn’t as much of an issue, non-waterproof boots may be a better option. People who tend to get toasty feet will find that the non-sealed boots allow for slightly more ventilation and breathability.
If that is the case for you, look for “water resistant” boots (as opposed to waterproof), which will be good for light rainfall. Or you can even buy neither waterproof nor water resistant if you don’t need the protection at all.
Unfortunately, this article is focused mainly on waterproof boot options, so I don’t have as many suggestions for water resistant and non water resistant options. Please mention some brands in the comments for me to check out!
On the other hand, you can buy a waterproofing boot spray or boot wax for boots that need more water-resistance. However, be aware that treating your boots with these products will never be as good as buying waterproof boots from the start (if that’s what you’re looking for).
The height of the boot doesn’t matter as much in milder winters/fall, because you will not need as much protection from extreme weather such as blizzards, slush, and hail. Instead, you can pick according to your preference in style.
For the sake of consistency, I am considering short boots to be boots that go just above the ankle. Midi boots are boots that go up about mid-calf, and tall boots go up closer to the knee.
I did my best to sort them all out correctly. However, there are several boots that do not fit these specifications perfectly. I have categorized these boots into where I believe they fit the best, but make sure you check the product description for exact measurements and details.
Waterproof: Shorty Boots
- Non-marking rubber lugged outsole with Wave-Siping for ultimate wet/dry traction
- **This is Sperry’s signature style, so if you don’t like this exact color and material, check out their website for even more options (e.g. with Thinsulate, and as a Midi boot).
- Insulated with Columbia’s patented thermal-reflective lining
- Rated -25°F (-32°C) with 200g insulation
- Rubber outsoles for traction
- Rubber lug outsoles
- A more girly version of Timberland’s signature style.
- Available in a variety of colors, or in fleece fold-down.
- Rated 35°F (2°C) with low activity, and 0°F (-18°C) with moderate activity
- Rubber chain-tread bottom for traction
- Rated to -25°F (-32°C) with 200g insulation
- KEEN.FREEZE rubber outsole for traction in cold conditions
- Also available in different colors for the older version of this boot.
- 200g insulation
- Durable TNF Winter Grip rubber outsole with IcePick temperature-sensitive rubber lugs for increased traction
- 200g insulation
- Durable TNF Winter Grip rubber outsole with IcePick temperature-sensitive rubber lugs for increased traction
- Rubber outsole for traction
Waterproof: Midi Boots
- 100g insulation
- Rubber grip sole for traction
- Available in a large variety of colors
- 200g insulation
- 200g insulation
- Durable TNF Winter Grip rubber outsole with IcePick temperature-sensitive rubber lugs for increased traction
- 200g insulation
- Durable TNF Winter Grip rubber outsole with IcePick temperature-sensitive rubber lugs for increased traction
Waterproof: Tall Boots
- 200g insulation
- Durable TNF Winter Grip rubber outsole with IcePick temperature-sensitive rubber lugs for increased traction
Waterproof: Fashion Boots
- Rubber sole for traction
Water Resistant Boots
- Fleece-lined
- PVC/Rubber/hybrid sole built with grooved cleats for traction
- Salt-resistant leather
- Based off the original 1460 Smooth Leather Lace Up Boots
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