The Most Comfortable Shoes For Skateboarding

There are many comfortable skate shoes out there, from bulky heavy cupsoles to more stylish lightweight vulcs. In general, cupsoles offer the most comfort while skateboarding. Their bulky shape and plentiful cushioning offers lots of support to those who need it.

Comfortable skate shoes are beneficial when you have sore feet or suffer a heelbruise recently. They also are better at absorbing impacts when skating big features. There is a downside, comfortable skate shoes usually offer less board feel. There are a couple of exceptions though which we’ll address shortly.

7 Most Comfortable Skate Shoes

It’s hard to tell from here what you exactly need, so I made a mix of skate shoes that offer lots of support, comfort, and a few that feel comfortable but still offer a lot of boardfeel. Comfort and most board feel you should definitely check out the Nike SB Ishod Wair and DC Kalis S.

For lots of support, both the éS Silo and DC Legacy Slim 98 are a great choice. The Nike Dunks Low and Etnies Joslin 2 are great for high impact skateboarding. The Dunks are also great for those with wider feet. Anyway, here are 7 comfortable skate shoes:

1. DC Legacy 98 Slim

DC Legacy Slim 98

The DC Legacy 98 Slims take cues from their 90s predecessors, albeit downsized to a slimmer silhouette and lightweight size.  This footwear is updated with its OrthoLite footbeds and UniLite midsole for improved comfort and cushioning of a running shoe.

The DC Legacy 98 Slim is a nostalgic bulky skate shoe that offers comfort, support and impressive board feel, grip and flexibility. It is great for high-impact skateboarding and daily use, but less suitable for technical skateboarding.

The shoe has a UniLite midsole arch and an OrthoLite insole, making it very comfortable and providing excellent support. The Legacy 98 Slim is not the most durable shoe, but it is comparable to an average skate shoe and lasts for about 60 to 80 hours.

The suede of the shoe can last for at least 40 hours, depending on the freshness of the grip tape and how often you flick. The shoe is available in multiple colorways and fits true to size, offering a snug fit.

The slim silhouette of the shoe compensates for the bulkiness, but it may not be for everyone. The DC Legacy 98 Slim is a fusion of past and present trends that make it a desirable footwear option, offering many possibilities to skaters and non-skaters alike at an affordable price.

2. Nike SB Ishod Wair

Nike SB Ishod Wair skate shoe

The Nike SB Ishod Wair is a cupsole, but the most flexible skate shoe on this list that still feels very comfortable. It’s also one of the more stylish skate shoes out there. Most find it to be a very comfortable shoe that provides a lot of impact protection.

Consider the Ishod Wair if I need a skate shoe that offers more board feel and impact protection for skating larger features. Compared to other brands, the cupsole construction of this shoe is surprisingly thin, which allows for more flexibility and a decent boardfeel while still absorbing shocks.

They fit true to size and are suitable for those with slightly wider feet, with a toe box that isn’t too narrow and gradually shapes to your feet.

The Ishod Wair isn’t the most durable shoe. They covered a part of the mesh with a plastic-like material that has a tendency to tear. While the mesh keeps your feet cool in the summer and looks pretty neat, I think canvas would have been a better choice.

The rather big tongue of the shoe is strapped with elastic bands and stays in place.

3. éS Silo

eS Silo skate shoe

The éS Silo is a retro-styled skate shoe that has been updated with modern features to cater to skateboarders. It has an STI Energy midsole foam, 400 NBS rubber outsole, thermothane quarter panel, herringbone tread design, and breathable mesh on the upper.

Fortunately, the Silo is less bulky than the classic 2000 model, with a rounded toe box and an elevated midsole, and offers ample arch support for your ankle. The shoe offers boardfeel, but it requires a long time to break them in. At first they feel rather stiff and you have to be patient before it becomes more flexible.

The STI Energy foam technology used by éS Skateboarding provides comfort and impact protection to the wearer. The éS Silo fits true to size, is lightweight, and comfortable to skate in.

The shoe is durable when made with suede instead of nubuck leather, which wears out fast. The éS Silo is a good choice when you need lots of support, but not great for technical tricks. Great for high-impact skateboarding though.

4. Etnies Joslin 2

Etnies Joslin 2

The Etnies Joslin 2 skate shoe is comfortable and offers excellent arch support with decent insoles and flexible Michelin soles that provide great board feel and grip. However, the shoe’s durability is a major issue, and after 50 hours of use, the lace protectors and toe stitching wear out quickly, making the shoe fall apart.

While the shoe looks bulky and wide, it offers a narrow toe box, making it easy to perform subtle moves while skating. The shoe’s impressive padding provides excellent cushioning and can handle impacts well, but the overall durability is subpar.

The shoe requires repairs after about 50-60 hours of skating. The shoe fit is true to size and offers extra-thick ankle padding for additional support. While the Etnies Joslin 2 offers many of the qualities one would want in a pro model skate shoe, its durability is a significant concern, especially given its high price.

5. Nike SB Dunk Low

Nike SB Dunk Low

The Nike SB Dunk Low skate shoe has an iconic style that originated from the original Nike Dunk Low model. The shoe has a sporty look rather than a traditional skate shoe look and has been popular for many years with a wide range of colorways.

The Nike SB Dunk Low skate shoe is Nike’s most comfortable skate shoe you can get. They are true to size and require a break-in period. The outsole has good grip but is reasonably flexible. It gets better but can affect performance.

The shoe has a unique shape with a rounded toe and suede that comes up straight in the flick area. It’s a bit of a bulky shoe and rather wide, especially near the toe box. The shoe has great cushioning features, which is why it’s on this list. It comes a removable and molded insole with Zoom Air unit in the heel and an EVA foam midsole for support and protection.

Nike SB Dunk Low skate shoe is true to size, has a good grip, and has a unique shape that can make it bulky and wide. The suede doesn’t last very long, and it didn’t make it to my list of most durable skate shoes for good reasons. You can make the Dunk skate shoe last longer by patching the ollie and flick holes.

Overall, this is a very comfortable skate shoe with great cushioning features but lacks flexibility and durability. Works well for those who need extra support but technical skaters probably won’t enjoy this skate shoe.

6. Adidas Tyshawn

Adidas Tyshawn

The Tyshawn skate shoe is one of most comfortable shoe Adidas offers. It has lots of cushioning and is highly impact resistant. This shoe is great for high-impact skateboarding but also offers enough flexibility for technical skateboarding.

The shoe has a narrow fit, which may require skaters with wider feet to go half a size up. I had to try multiple pair before finding the right fit. The outsole is quite flexible for a cupsole, though not as flexible as a vulcanized shoe.

The suede is of extreme quality and does not fade easily. The shoe provides ample support and stability, with additional padding on the tongue directed towards pressure points. They feel secure and give a confidence boost from the moment you step on your board.

Other than that, it’s a stylish skate shoe and just looks good. The insoles aren’t terrible but could use some improvements. The Adidas Tyshawn are a bit more expensive than average but worth it for those that need a durable, comfortable shoe that offers lots of impact resistance.

7. DC Kalis Vulc Mid S

DC Kalis S mid vulc

The DC Kalis S is a modern take on a classic skate shoe and a tribute to Josh Kalis. The shoe features a super suede upper, ghillie lace pattern, long-wearing rubber outsole, UniLite midsole, low-cut form, and the DC pill pattern tread.

The Kalis S offers decent board feel and grip and is more flexible than the Legacy Slim 98 we mentioned. However, like most bulky DC shoes, it requires a break-in period. The shoe’s bulky design is off-putting for some, although it has a sleeker Kalis OG design.

The shoe comes in six color combinations and has Unilite midsole padding, which provides cushioning, support, comfort, and impact protection. The shoe is durable, with an abrasion-resistant outsole and a super suede toe.

The Kalis S is less durable compared to the DC Legacy 98 Slim, especially when you flick your board a lot. Overall, the DC Kalis S is a very comfy skate shoe that also provides excellent grip and flexibility.

The cushioning could be a bit better but it’s a vulcanized shoe so you get more flexibility. This skate shoe is true to size with normal width and length.  Despite the big and bulky exterior, it fits snugly to your foot.

What Makes A Comfortable Skate Shoe?

It really comes down to the shape of the shoe, the cushioning, and support. Many technical skaters want shoes that perform but typically street skate shoes aren’t always comfortable. Your best bet is a cupsole skate shoe because they have thicker outsoles and more padding near the heel area. They also have more arc support and impact protection but offer less boardfeel.

The Right Size Skate Shoe

You don’t want a skate shoe to feel too loose or too tight. You need a shoe with a snug fit. Even the time of day makes a difference. In the afternoon your feet might swell a bit compared to the early morning, this impacts the size of your feet and how a skate shoe fits.

A skate shoe that is too tight will hurt. Even when you don’t feel any pain and the suede expands a bit, it will still cause your shoe to wear faster. Skate shoes don’t last long if they fit too tight.

If your foot is pressing against the suede and you flick your board, there will be more friction. Your foot will put more pressure on the suede harder than a less tight fitting shoe. Avoiding a tight fit is important and will impact your ability to control the toe area when flicking your board.


Comfortable skate shoes should have extra cushioning added to different parts of the shoe. Extra foam, for example, on the insole, padding around collar, tongue, and heel will make a shoe much more comfortable. Extra padding also helps absorb the impact of landing tricks and can prevent injuries to the feet and ankles.

Wide and Narrow Cuts

The cut of the shoe often determines how tight a shoe fits. Some skate shoes also have a pointy and rather narrow toe box, like many Nike skate shoes. The with of a shoe cut is not set in stone and varies per brand and model. Your best bet is to go to your local (skate) shop and see what works for you.


Look for perforation holes on the side and or upper of a skate shoe. If you skate in warmer conditions or quickly get sweaty feet, you want your feet to cooldown. Without some sort of ventilation, your feet might swell and obviously they won’t smell pleasant. While everyone’s feet sweat when skateboarding, some do more than others resulting in stinky skate shoes.

Some skate shoes offer a different mesh on the side which often is made of canvas, a breathable and flexible material. Canvas in the right areas can make a vast difference.

The Nike Ishod Wair, for example, has a plastic mesh on the side which maes it a very breathable shoe (but also less durable). Thicker padding also contributes to sweating feet if there is a lack of ventilation.


Skate shoe insoles

Insoles are important, but not all brands offer great insoles. Insoles quality varies and you can even get expensive after market insoles up to 80 bucks (which is ridiculous FP Insoles!). If you want to replace your insoles, I would recommend Dr. Scholl’s insoles. They’re cheap and they work.

Anyway, some insoles are made of durable EVA, which is a plastic heat resistant material that is lighter and more flexible than rubber. Most skate shoes offer the ability to remove and replace them because they often are less effective after 2 or 3 months of skateboarding.

Other materials that are often used in insoles are foam, gel, cork, and even leather. Foam offers the most comfort and gel is great at absorbing shocks. Nike has these gel pads, for example:

Nike SB insole

A good insole makes a skate shoe much more comfortable, so maybe you don’t even need new shoes, just replacing the current insole can make a tremendous difference!

That’s it, thanks for reading and check out our other skate shoe articles, there are plenty!

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Ruben Vee

I love skateboarding but my age is catching up. I decided to use my experience to skate less and write more. 20 years of skateboarding allows me to offer original and unique insights for many styles of skateboarding.