Cushioning is one thing that chukka boots usually lack. There is usually some cushioning built into the outsole, which is usually rubber or crepe rubber. Both materials offer some minimal shock absorption and cushioning to protect your feet. Some chukkas come with cushioning built into the upper by means of padding and into the footbed by means of the insole and midsole.

Padding
Some chukka boots come with padded leather collars, tongues, and uppers. Depending on the material used in the padding and what you’re using the boots for, this padding can cushion some rubbing of the upper against your foot and ankle. However, if the padding is too firm or hard, then you would probably want to pass on that chukka, as a hard padding could hurt your ankles and Achilles tendons.

Insole
Generally, chukka boots don’t have much by means of cushioning in their insoles. When you are looking for a new chukka boot, always check the insole to confirm that it will offer you enough cushioning to absorb the shock from each of your footsteps. Some manufacturers have invested in lightweight and thin cushioning technologies in their insoles, so it is possible for you to find a chukka with ample cushioning.

Midsole
Some chukka manufacturers include midsole cushioning and support technologies, but not all chukka boots will have it. If the insole is cushioned enough and the outsole is sufficient for shock absorption, then not having a midsole should be fine. Ultimately, you would need to try them on or check out what other people have said about the boots you are considering purchasing before you buy.

Outsole
Chukka boots all come with a crepe, rubber, or synthetic outsole. All of these outsole materials offer shock absorption and cushioning, but some are better than others. Of these, crepe outsoles may offer the most comfort, but they aren’t very good for heavy outdoor use. Rubber and synthetic outsoles offer a little less cushioning and shock absorption, but they are much more durable and long-lasting

It’s important to consider the fit and sizing options in your chukka boots. Not every chukka boot is designed with your foot shape and needs in mind. Some are too narrow, others have too large toe boxes, and so on. As such, you should spend some time researching or shopping around for the chukka boot shape and size that suit your needs the most.

Width Size Availability
Not all chukkas come in wide sizes. If you have a wide foot, then you need to consider whether or not this boot comes in a wide or extra wide size which would fit your feet properly. Wearing chukkas which are too tight could lead to injury and toe deformities, neither of which is fun.

Similarly, wearing chukkas which are too large can also result in foot injuries or worse, so it’s important to find the chukka which fits your foot properly.

To confirm that the boots fit properly, you should try them on and walk around in them a little bit if you’re buying them from a store. If they slide around or slip off your foot, they’re too large. If they squeeze and cause pain, then they’re too small.

Toe Box Shape
Most chukkas come with a rounded point forefoot. However, some have less drastic points than others. For wide feet, it’s best to look for one of these less pointed forefoot areas to protect your toes from injury and pain. The best chukkas provide enough space in the forefoot for your toes to spread out naturally without pain or discomfort.

Unlike with cushioning, chukkas generally excel in stability and support. While they may not be the best at providing ample arch support, the upper is always firm and prevents rolling an ankle or your foot. However, there is such a thing as too much support, so it would be in your best interests to find an upper material which provides some flex to give you a more comfortable stride.

Upper Materials

Leather
Leather is the firmest and offers the most support and stability. If you are looking for a firm, smooth boot, then a leather upper is the best fit for you.

Suede
Suede is another type of leather which can be just as firm and supportive. However, suede is made with the softer parts of animal skins, so it’s softer and has a fuzzier texture than leather generally has.

Synthetic
Synthetic uppers are entirely man-made and include no animal products whatsoever. Depending on the materials used and the design of the upper, synthetic uppers can be the most flexible, but they are also quite capable of providing ample support and stability.

Outsole Materials

Rubber
Rubber is generally quite supportive and offers ample cushioning- the best of both worlds. Rubber is a firm material which absorbs shock well without sacrificing flexibility. Rubber outsoles will bend and move with your natural foot movements.

Crepe
Crepe outsoles are more flexible than rubber and they provide optimal shock absorption. However, they are generally less durable than rubber or synthetic outsoles.

Synthetic
Synthetic outsoles have the most potential for flexibility, but they can also offer optimal support. It depends on the type of outsole and the manufacturer. Always do some research or try on the chukkas before you buy to ensure that you are getting the boot that offers the right amount of support and flexibility for you.

All shoes need to provide at least some traction. However, it’s important to get the most traction possible if there’s any chance that you’re going to walk on a slippery-smooth, wet, or uneven surface- which describes most situations, doesn’t it? Therefore, you need to confirm that your new chukka boots come with the best traction possible. Unfortunately, as these are dressier shoes, they don’t come with as much traction as sneakers and hiking boots.

Here are some things to consider that contribute to the traction capabilities of your prospective chukka boots:

Outsole Type
Of the types of outsoles regularly found in chukka boots, rubber, and synthetic outsoles generally offer the most traction. Crepe outsoles offer less in terms of traction, but that doesn’t mean you should avoid a chukka boot with a crepe outsole. The biggest determiner for how much traction a boot is going to offer is actually the tread pattern.

Tread Pattern
Tread patterns in your boots can make or break their traction capability. The best tread patterns for traction and slip-resistance include many thin perpendicular lines throughout the entire outsole, but most of the outsole is still pressing against the ground for optimal grip.

In general, chukkas are not designed with temperature regulation in mind. They’re a simple dress boot, but many manufacturers are investing in temperature regulating technologies to use in their chukka boots to increase the comfort and protection which they offer. A few such examples include breathability features, linings, and waterproofing.

Breathability
Some manufacturers of chukka boots use perforations in the upper of their boots to provide some airflow in and out of the boot. However, most don’t include perforations, as it detracts from the classic chukka look. In general, the materials used in the upper of chukka boots are not breathable by default.

Linings
Some chukka boot manufacturers invest in warm wool upper linings while others invest in cool gel linings. Consider the environment that you will be using these boots in before you decide. If you are going to be on your feet all day in a hot environment or doing a lot of physical activity, you would probably want to steer clear of the warm linings. Gel linings are usually incorporated into the insole, so the gel linings keep your feet cool while also providing cushioning and comfort, so they’re great for activities requiring you to be on your feet all day.

Waterproofing
Waterproofed chukka boots are great if you are going to be in a wet environment part or most of the day. If you spill something on a waterproofed chukka, you won’t ruin the leather or suede. Dry feet are usually cooler than wet feet and dry feet develop fewer blisters.

Rainproofing
A subcategory of waterproofing is rainproofing. Rainproofing only protects your chukkas from light exposure to water, such as when it is raining or you spill something on them. Rainproof chukkas are not designed to be submerged in water and doing so could ruin your leather or suede upper.