Given the title of this guide, it is reasonable to assume that all of the options we have laid out in our list are boots. They are meant to protect you from cold and wet weather conditions, while at the same time helping you look stylish.

As you have seen, there are many different types of boot styles. In this section, we will talk about each one we have here, and about their pros and cons. Let’s begin!

• Ankle: Ankle-height designs are arguably the most popular type currently on the market. The reason for this is that they are easy to pull on and easy to take off, and people who have calves which are too thick or too thin don’t have to struggle with finding the right fit for their leg.

  Ankle boots provide just as much weather protection as taller options, and they also keep your feet warm. The bonus of having your ankle surrounded by a shaft is that it is supported and stabilized on all sides, minimizing injury from twisting it or spraining it.

  The downside to an ankle boot is that rain or snow might still get in through the top of the shaft and that it doesn’t protect your leg from the cold. However, if you are living in a place with dry, not-so-freezing winters, and don’t want to be bothered with finding the right width for your calf, an ankle-height is the perfect solution.

• Mid-Calf: Taller than ankle and lower than over-the-knee, we have the standard mid-calf option. These are also classic and can be found almost anywhere. Those who don’t mind searching a bit longer for a size that fits their calves get the benefit of keeping their legs warm and protected as well.

  Mid-calf boots are particularly useful because in those cases you can choose whether you want to have an ankle model or one that covers most of your lower leg!

• Over the Knee:
  Finally, we have the tallest version that is still practical to wear, the OTK design. While these have some function in the form of fishing boots, usually they come as a fashion statement, a means to draw everyone’s attention. OTK boots are created to be eye-catching, sexy and empowering, and as such they are more geared towards style than towards functionality.

  The downside of an OTK design is that it is difficult to find one which is easy to slide on, which doesn’t pinch your leg or sag or bunch up in weird places, and which looks flattering. However, if you have an opportunity to try a design on, don’t hesitate! You might just encounter a gorgeous OTK that you want to take home. After all, thanks to the folding cuff option, you can always make these appear lower than they actually are.

Aside from the question of how good a design looks on you, we also have to address another important aspect - if it is comfortable or not. So many times we fall for an attractive style, one that goes well with those jeans or that cute little skirt we have, but then it turns out we can’t even wear our new shoes because of how much they hurt.

This is why we have to dig deeper into what makes these designs comfortable, and what you can look for to increase your chances of being able to wear them over extended periods of time.

• Upper: Because so much of this footwear style is the upper - especially if it’s a mid-calf or an OTK design - the materials the upper is made of are extremely important. They need to be soft and malleable, to mold to the shape of your foot and leg, but also to be solid enough to provide support, to stay up and not stretch out or lose shape over time.

  The best material footwear can be made from is genuine leather and genuine suede. These natural materials are breathable, flexible, conforming and durable, and really a great choice all around.

  Synthetics, like faux leather and suede, are not as high in quality. However, if you are vegan, or are interested in animal-friendly designs, then synthetics are definitely the way to go. These designs are also less expensive than genuine leather ones, meaning that your budget won’t suffer, either.

• Lining: From the upper, we’re moving inside the boot and taking a moment to see what the interior is made from. The lining is equally as important as the external materials because this is what comes in contact with your feet and legs, and perhaps even your skin if you’re not wearing socks. You want the lining to preserve warmth, but also to be soft and comfortable, and to not cause any chafing or abrasions.

  Fluffy options, such as fur, faux fur, wool or shearling, are great for providing plush comfort. There are also fleece linings and even leather ones which are just as good in making sure that your feet are properly ventilated and comfy.

  However, both in the case of the lining and the upper, make sure to check if the materials are too stiff. If that is the case, the shoes may need some breaking in before they become comfortable enough for wearing it all day.

• Footbed: The last, but not the least feature that concerns comfort is the footbed of a design. This is where true support lies. Footbeds come in many shapes and forms, made from many different materials, and here we will talk about the most common versions.

  We’ll start with cushioned footbeds. These have added padding to them, which quite literally cushions your feet, adds a bounce to your step and provides shock absorption. Cushioned footbeds are usually made from memory foam or EVA; they help minimize the pressure put on your joints, and allow you to stay on your feet for longer.

  The second type of a footbed is a molded footbed. This type has contours which correspond to the lines of the foot, and thus provide an addictive sort of comfort. Molded footbeds also often have arch support, which is a vital detail in reducing foot fatigue and preventing a condition called flatfoot.

  Whether you will go for a cushioned footbed, or a molded one - or both - is all really up to you. Remember that comfort is subjective, as most other criteria here, and if something works for others doesn’t necessarily mean that it will work for you. Choose carefully, and if something doesn’t feel right when you’re trying the shoes on, it may be wise to think a little bit more about the purchase.

As we mentioned before, the purpose of boots is to protect you, to keep you warm and dry and comfortable in cold days covered in rain and snow. Not all designs do this, of course - some are more fashion than protection - and this is why we have also felt the need to include Weather Resistance in our Criteria.

Designs in our list can be divided into those which are meant for extreme conditions, and those which are more for dry autumns than for any real trudging through the snow and the slush.

Thus we have our Extreme group: the Sorel Emelie, the Columbia Cityside, the Timberland Teddy and similar. These are options which are waterproof, designed to keep out any and all signs of moisture. They are also lined with insulating materials, with the purpose of preserving warmth inside the design. Their outsoles are made from non-slip compounds, which also have deep grooves or even lugs at the bottom to keep you steady and stable on all types of slippery surfaces.

With these options, you will be able to take on pretty much anything that winter throws at you.

On the other side of the coin, we have less sturdy, more stylish choices such as the Cole Haan Raina Grand. When it comes to weather resistance, these are not as useful as the Extreme group - they are made from high-quality materials, but they are not waterproof and don’t do much in the way of providing you with warmth.

We’re not saying that any one group is worse than the other. We’re merely pointing out a difference in some of our models, and leaving you to decide which one you prefer. If you’re looking for a solid, protective winter option, then choose from the Extreme category. However, if winters in your area are not as bad and you prefer something more fashionable, then the latter, more refined group of designs is the better choice for you.

When we buy a design that we love, we expect to be able to wear it on as many occasions as possible. We want to feel confident, want to show it off to our friends and family, and we want our purchase to pay off. Because what is the point of a shoe if it will just sit and collect dust in the closet?

Foldover boots have versatility built right into them. For the price of one, you get two different versions of the same shoe - one taller and sleeker and one shorter and with its plush and/or colorful lining exposed. In that regard, all of the items on our list are the same - all of them deliver that possibility of changing up your look at a moment’s notice.

So we looked beyond that, at the overall aesthetic of the designs, and judged their versatility based on that. We considered in what conditions a design can be worn in, as well as what outfits it matches the best.

It is no wonder that the smoother, more streamlined products, such as the Timberland Teddy and the Ugg Bailey Button came out on top. These are really easy to pair with jeans and leggings and even shorts or skirts if you have thick enough tights to wear underneath. They are exceptionally trendy this season - and will be in the future seasons as well - and they will only add to your already fashion-forward collection of footwear.

Less versatile are the bulky, protective-but-not-attractive winter options, like the Sorel Emelie, the Columbia Cityside and the Skechers Grand Jams Unlimited. These are great for harsh conditions, for exploring trails and braving snow-covered city streets. However, they lack elegance and are usually only worn either out of necessity, or as a handy design for outdoor activity.

All that being said, we can’t end this section without saying that just because a design is low or high on our list regarding versatility, doesn’t mean that it should stop you from wearing it wherever you want. If the dress code allows, and if you are comfortable, wear your new shoes in any event you wish!

Durability as a characteristic is determined by a myriad of factors - the materials the footwear made from, the methods used in their construction, the conditions they're worn in, the frequency of use and similar.

Fortunately, almost all of the options in our list are made from high-quality materials. And we mean, extremely high-quality materials. These ones which are not are made from synthetic leather and suede rather than genuine ones, which decreases their durability a smidgen compared to the other designs.

When it comes to construction, one option stands out among the rest, and that is the Dr. Martens Aimilita. This pair is made using the Goodyear welt technique. The Goodyear welt method is widely regarded as one of the best when it comes to constructing footwear, mostly because designs made like this are waterproof and easily resoled, making them last for literally decades. Consequently, shoes made using the Goodyear welt technique are more expensive than others.

In terms of construction, even though the other items are made using machinery in an industrial process, they aren’t that far behind. Due to the solid, high-grade materials they are made of, they will also last years, as long as you keep the genuine leather and suede adequately clean and conditioned.