Wildling Shoes Chestnut Review | Good Cold Weather-Friendly Barefoot Shoes?

Wildling Shoes makes a wide range of minimalist shoes for various contexts. As someone who loves high-top shoes, when I first saw the Wildling Shoes Chestnut, I fell immediately in love with this shoe’s clean, refined appearance.

For casual wear, I’ve enjoyed the Wildling Shoes Chestnut, I like this shoe’s performance for the most part. However, there are a few cons to note about this shoe and contexts where it falls short, which I’ll discuss below.

In this Wildling Shoes Chestnut review, I’ll cover various topics to help you decide if these shoes are a good fit for your needs.

Who Should Invest In the Wildling Chestnut?

The Wildling Shoes Chestnut can be a good minimalist shoe to explore for those who want a high-top minimalist shoe for daily wear. This shoe has a casual and refined appearance and can be easily styled with different outfits.

I think for day-to-day wear and even business casual contexts, the Chestnut can be a comfortable and casual option to explore. Another perk that I like with these shoes is that they’re handmade which is also a unique perk and pro of these shoes.

On top of being handmade, Wildling Shoes also states that these shoes are ethically made with natural materials, so if that’s high on your priority list for minimalist shoes, I think you’ll also enjoy this characteristic of Wilding Shoes Chestnut.

Regarding width, these shoes are plenty wide to accommodate most foot anatomies and they have a fair amount of upper volume. If you’re after width and a good-looking shoe for day-to-day wear, then the Chestnut can be a good option to explore.

That being said, this model doesn’t have the best long-term durability and they fall short in inclement weather so they will be a little limited regarding their daily wear versatility, and I’ll discuss this more below in my cons section.

Wildling Shoes Chestnut

$139

4.4

Versatility

4.4

Durability

4.3

Quality

4.5

Best For

• All-Season Use (Dry Climates)
• Casual Wear
• Business Casual Wear
• High-Top Shoe Lovers

Falls Short

• For Long-Term Durability
• For Wet Climates

Shop Wildling

Wildling Chestnut Pros

Over the course of my testing and review process with the Wildling Shoes Chestnut, I found multiple pros to like about this model.

1. Good for Daily and Business Casual Wear
2. Nice Width Through the Forefoot and Midfoot
3. Handmade With Natural Materials

The first aspect to like about the Wildling Shoes Chestnut is its performance for daily, casual, and business casual wear. I bought the Chestnut because I really enjoyed its refined appearance and neutral colors.

I find that it’s easy to style this shoe with different outfits and that it works well in a pretty wide range of contexts. You can run errands in these shoes, wear them all day, and rock them to the office and they’ll look pretty good.

Granted, you’ll know your office’s dress code better than me, but I’ve definitely worked in some editorial settings where this shoe’s appearance would certainly fly as being business casual.

I also like the internal wool construction of these shoes because it gives them a nice level of comfort for daily wear. They’re an easy shoe to have on all day and can work well for multiple seasons.

The second perk of the Wildling Shoes Chestnut is the width through their midfoot and forefoot. If you’re looking for maximal width in your shoes, then the Chestnut should deliver on that promise.

This model is slightly wider than Xero Shoes and Vivobarefoot models, so for toe splay and width-focused comfort, these will work well. I also like the amount of upper volume that you get with these shoes, as most foot anatomies, even super thick feet should have adequate room in these shoes.

The final perk that I have with the Wildling Shoes Chestnut is the fact that they’re handmade with natural materials. I think this adds a cool artisanal feel and vibe to these shoes which I wish more companies would adopt.

I also like the fact that Wildling Shoes lists all of the materials used in these shoes and what percentages of each are used. This helps add depth to the “why” behind these shoes and I like that Wildling Shoes isn’t super vague about their “recycled materials” like other companies.

Wildling Chestnut Cons

While I enjoy the Wildling Shoes Chestnut, for the most part, there are a few cons to note about this shoe before investing in them.

1. Do Not Come With Insoles
2. Not a Great Shoe for Wet Climates
3. Long-Term Durability Can Lack, Relatively Speaking

The first drawback that I have with the Wildling Shoes Chestnut is the fact that they don’t come with insoles. This isn’t necessarily a bad thing for most consumers, however, it does add an extra purchase for some.

For example, for the Chestnut, Wildling Shoes recommends that narrow feet should use an insole in this model. The additional insole if you go through Wildling Shoes will cost you anywhere from $7.90-$11.90 USD, and this is on top of this shoe’s price of $139 USD.

On top of this, since the internal lining of this shoe is built with wool, I’ve started to notice mine fraying a little bit from the friction of daily wear and whether I’m barefoot or using socks. An insole could prevent this, so I do wish Wildling Shoes included them with the Chestnut.

Another drawback with the Wildling Shoes Chestnut is their ability to perform in inclement weather. This model is designed for daily wear, but not every type of daily wear and I’d highly suggest not using these shoes in rainy or damp climates.

Since this shoe’s outsole doesn’t cover the entirety of this shoe’s sole, I noticed that the material absorbed water pretty easily when I wore these on a day when it was a little damp outside. For context, this was on a post-snow day so the ground was damp.

If you want these for everyday use, then you may be a little limited as you’ll want to avoid wearing these on poor weather days. I’d suggest rotating these in with other shoes, especially pairs that you can beat up on rainy days that will fare better in that context.

My final drawback with the Wildling Shoes Chestnut is that their long-term may not compare to other minimalist shoes on the market. This shoe’s wool internal lining and midsole construction could be issues down the road as you put more miles into these shoes.

As mentioned above, this is definitely a minimalist shoe that you’ll want to rotate in with other models to prolong their lifespan. I like the super minimalist feel of this shoe’s outsole and midsole, but that comes at a cost of durability in some contexts.

For example, shoes with full rubber outsoles and thicker upper construction will likely last longer than this shoe, and I’m already starting to notice the outsole of my model lipping a little bit on my right shoe.

I think if you’re wanting a minimalist shoe for a lot of walking or for wearing in different climates, then you’ll want to explore options that will give you more durability per your investment.

Performance and Styling

To break down the performance of the Wildling Shoes Chestnut, I’ll cover how these shoes perform in different settings. I’ll discuss the Chestnut’s performance for day-to-day wear, and walking, and how they fare for multi-season use.

I’ll also highlight some ways that I like to style the Wildling Shoes Chestnut. Do note, I’m not by any means trying to claim I’m a fashion expert, but I did want to share some outfits that I regularly rock these with.

Testing the Wildling Shoes Chestnut for Walking and Daily Wear

For daily wear and walking, I’ve enjoyed the performance of the Wildling Shoes Chestnut, for the most part. On a daily wear basis, I like the Chestnut for three key reasons. First, its appearance is a hit, especially if your style is more subtle.

I like that the Chestnut comes in neutral colors and that it can easily be styled with pants and shorts. For day-to-day use and some business casual wear contexts, the Chestnut delivers a strong performance.

Second, I like how much width you get in this shoe’s forefoot and midfoot. The width of this shoe gives them a comfortable feel and for walking and standing, I like how easy it is to move my toes and let my feet do their thing.

Third and lastly, you get a nice level of articulation with this shoe. If you want to get as close to the ground as possible in daily wear contexts, then you should resonate with the Chestnut. This model feels very minimalist in nature which I like.

For walking, this shoe works well for short to moderate mileage walks, but it does have some limitations. If you’re wanting a shoe for purposely long walks or for wear in inclement weather, you’ll want to steer clear of the Wildling Shoes Chestnut due to long-term durability concerns.

Testing the Wildling Shoes Chestnut for Multi-Season Use

When it comes to the multi-season use of the Wildling Shoes Chestnut, they can be a pretty good 4-season shoe within reason. Unlike other minimalist shoes that can run cooler through fall and winter, the Chestnut provides a nice level of warmth.

For example, on days when the temperature is sitting around 30-40 degrees Farenheight, this shoe is plenty warm even when wearing fairly thin socks. On that note, once the temperature drops below 40 degrees, I will wear socks with these shoes.

If you’re rocking these regularly without socks and insoles like me, then you’ll notice your feet start to get cooler in these contexts, so socks are definitely the play. The internal wool construction does a good job with thermoregulation overall.

For warmer days, I’ll wear these sockless and they work well. I wouldn’t want to wear them for a ton of mileage on warm days, but if you’re wearing them out and about and spending the majority of your day indoors in an office, they’ll work well.

Styling the Wildling Shoes Chestnut

When it comes to styling the Wilding Shoes Chestnut, I find them pretty easy to wear with most outfits. For example, I’ll wear them out and about with shorts when I’m walking the dogs or grabbing a coffee, and I’ll also dress them up with pants.

I think if you’re wanting a shoe that can be worn with jeans and other dark pants, then the Chestnut can be a good option. With khakis, I’m still hit or miss on them whether I like how they look, to be honest.

Wildling Chestnut Sizing

For the Wildling Shoes Chestnut, I think most will want to size down a half-size to a full-size. Since Wildling Shoes are built in Europe, you’ll have to use the US/Canada-facing side of the site which converts sizes accordingly.

On Wildling Shoes site, they suggest that this model fits true to size based on their Fitkit tool. Alright, so I took that statement as these shoes fit true to size, so I went with my normal size and found this shoe to run nearly a full size long.

I’m curious if there’s a little discrepancy between their EU and US sizing, as even the US men’s and women’s sizes are a little inconsistent. For example, typically there’s a 1.5 size difference between men’s and women’s shoes.

On Wildling Shoes’ site, some men’s and women’s sizes convert to being 1 size apart (ex: 10M/11W) while others are only .5 (ex: 13M/13.5W). Before you invest, I’d highly suggest using their Fitkit and then potentially going down depending on your fit preferences.

• Wildling Shoes Chestnut Sizing Thoughts: Size down a half size to full size.

In addition to running long, Wildling Shoes also recommends using an insole for narrow feet as the volume of these shoes runs pretty large. If you have narrow feet this is also something to consider as you’ll have to spend more than $139 for these shoes.

If you have additional sizing and fit questions on the Wildling Shoes Chestnut, drop a comment below.

Price Breakdown

For the Wildling Shoes Chestnut, you can expect to pay $139 USD. Compared to comparable minimalist shoes, this price point runs a little on the higher end, but I don’t necessarily think that’s a bad thing.

For example, I think the fact that every shoe is handmade in Portugal can help justify the slightly higher price point. Plus, Wildling Shoes claims to use ethical construction processes with natural materials, which I also like.

I think if you’re wanting a shoe to rotate in with other casual wear minimalist shoes, then the price of the Wildling Shoes Chestnut makes sense. In this context, this will also prolong this shoe’s lifespan which will make your investment last longer.

Conversely, if you want a single shoe to wear every day, you may want to explore other minimalist shoes as this model will be slightly limited based on the weather that you’re experiencing.

Wildling Shoes Chestnut

$139

4.4

Versatility

4.4

Durability

4.3

Quality

4.5

Best For

• All-Season Use (Dry Climates)
• Casual Wear
• Business Casual Wear
• High-Top Shoe Lovers

Falls Short

• For Long-Term Durability
• For Wet Climates

Shop Wildling

Construction Details

One of the cool things about Wildling Shoes is that every pair is said to be handmade. Below are some of the most important construction details to know about the Wildling Shoes Chestnut.

• Heel-to-Toe Drop: 0mm
• Weight: 
• Removable Insole: Doesn’t Come With An Insole
• Canvas Upper (60% wool, 40% hemp)
• Felted Wool Loden Lining/Midsole
• Outsole (synthetic rubber, recycled materials, silica, and recycled cork)
• External Heel Loop
• Microfiber Edging
• 6 Core Metal Eyelets

If you have additional construction-related questions about the Wildling Shoes Chestnut, drop a comment below.

Takeaway Thoughts

There’s a lot to like about the Wildling Shoes Chestnut and I appreciate the artisanal nature of the shoes. These shoes look pretty good and have a naturally refined appearance to them.

I could see the Wildling Shoes Chestnut performing well as an all-season casual wear minimalist shoe in dryer climates. Additionally, I could see these being comfortable shoes for office wear based on your dress code.

My main complaint with the Wildling Shoes Chestnut is that they fall short for inclement weather and their long-term durability may not be the best compared to other minimalist shoes.

If you have additional questions on the Wildling Shoes Chestnut, drop a comment below or reach out to me personally via Instagram (@jake_boly or @that_fit_friend).