In-Depth Wolf and Shepherd Shoes Review

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If I’ve said it before, I’ve said it a thousand times: 

Shoes are the secret weapon of style. 

There’s no easier or more effective way to elevate your appearance and take your look from average to attractive than by throwing on a sharp and stylish pair of shoes. 

The problem is that some of the most dapper and stylish shoes also tend to be the least comfortable. 

Dress shoes, of course, have always been notoriously painful to wear. 

But what’s even worse, at least in my opinion, is that casual shoes like loafers can be just as bad. 

Man wearing brown Wolf and Shepherd Crossover Loafers
Wolf & Shepherd is founded on the idea that shoes can be both stylish and comfortable. But… can they?

A good pair of driving shoes or penny loafers may look relaxed and laid back, but most of them will give you blisters if you wear them for too long, or walk too far in them.

So I was extremely curious to learn about Wolf & Shepherd footwear, a shoe company founded on the idea that shoes can be both good-looking and good-feeling all at the same time. 

I recently spent a few weeks going for long walks in three of their shoes to find out how they stack up in terms of style, comfort and quality. 

Read on to learn the full results of my thorough Wolf & Shepherd review and find out if their shoes are really up to snuff. 

Full Disclosure

This review came about because Wolf & Shepherd reached out to ask if I would review their product.

As I always do when brands reach out, I told them I’d be happy to try a few pairs, but only if they were comfortable with me writing a thorough, honest and transparent review.

They agreed and sent me the shoes, and the opinions that follow are my own, as are the (lame) jokes, (random) asides and (grossly over used) parentheses.

In Review: Wolf and Shepherd Shoes

(After Trying Three Separate Pairs of Wolf and Shepherd’s Shoes)

Overview of Wolf & Shepherd 

Wolf & Shepherd Logo

Wolf and Shepherd was the brainchild of Justin Schneider, a former track and field athlete at Notre Dame who later became a shoe designer for Adidas. 

While working at Adidas, Schneider noticed a significant gap in the footwear industry:

There were plenty of stylish men’s dress shoes that looked great, but were uncomfortable and hard to wear. 

On the other end of the spectrum, there were plenty of comfortable athletic shoes that performed at high levels.

But they wouldn’t pass muster in situations that call for a formal shoe, like at the office or a special occasion. 

Wolf and Shepherd founder Justin Schneider
Wolf & Shepherd founder Justin Schneider

At the time, there weren’t many shoes that managed to satisfy both needs, so Wolf and Shepherd was founded to fill that gap. 

Schneider created a prototype by merging an old pair of Italian leather dress shoes with the supportive rubber soles of sneakers… 

…and then the crazy motherf@cker went out and wore them to run a 5K. 

Somewhat surprisingly, the prototype held up quite well, prompting Schneider to found Wolf and Shepherd with the goal of making comfortable dress shoes that look as good as they feel. 

So, do Schneiders shoes work as well as his original prototype? 

Wolf and Shepherd Review #1: The SwiftKnit Derby 

Wolf and Shepherd Swiftknit Derby Shoes

The first pair of Wolf and Shepherd’s shoes that I tried was their SwiftKnit Derby, a sort of hybrid between a traditional derby shoe and a sneaker. 

The original prototype that founder Justin Schneider used for his 5K merged the leather upper of an old pair of dress shoes with the sole of a running shoe, and a few W&S shoes still use a similar approach. 

(I’ll discuss two of them in detail below.) 

But the SwiftKnit has a knit upper made from recycled polyester, which makes it distinct from almost any other type of shoes. 


Sharp Toe Shape
Toe shape of Wolf and Shepherd Swiftknit Derby shoes
The Swiftknits have a toe shape that’s comparable to most dress shoes, giving them a more refined look

The first thing I noticed about the SwiftKnit was how unique it looked. 

The thick foam heel gives it a distinctly athletic vibe, but it has a refined toe box that you’d expect to see more on a line of luxury shoes than on athletic or casual shoes. 

The result is a unique dichotomy that immediately makes the SwiftKnit more eye-catching and (in my opinion) more dapper than a standard sneaker. 

The (Handsome) Devil is in the Details 
Leather details of Wolf and Shepherd Swiftknit Derby shoes
Small details like the leather extras add a touch of refinement that helps elevate the Swiftknits

The next thing that stood out for me about the SwiftKnit are the small but handsome details the footwear designer has added. 

The pull tabs on the back are practical, making it easy to slip the shoe on without having to untie it. 

But they’re also made from premium leather, which combines with the leather details that have been added to the tongue and the upper part of the cushioned outsole.

All in, they lend the shoe a refined sense of style that elevates its overall appearance. 

Color Me Impressed 
Color options of Wolf and Shepherd Swiftknit Derby shoes
The Swiftknit is available in 10 colors total, of which I tried two

I sampled SwiftKnits in two of the 10 available colors: navy and gray

Both colorways perfectly matched the shades that were presented on the website, which was a relief. 

Real life color shot of Wolf and Shepherd Swiftknit Derby shoes
The color of the shoes matched the photos on the website, much to my relief

I find there are a whole bunch of online shoe companies nowadays that attempt to color correct the photos on their websites, and end up misrepresenting the color of their shoes as a result. 

So it was nice to see the exact colors I expected when I opened the box. 

The other thing that struck me about the colors was how well the leather detailing complements the shoe’s primary color. 

With brown leather accents, the navy shoes capitalize on one of the most classic color contrasts in menswear, while the gray pair goes for minimalism rather than contrast, keeping the leather accent pieces gray 

As someone who’s written extensively about the advantages of the blue-and-brown combo, I preferred the contrast on the navy shoes. 

But even I have to admit that the gray version looks sleek as hell – and possibly even a little more sophisticated. 

Comfort & Quality 

As nice as the SwiftKnits looked out of the box, the real test came when I tried them on and hit the pavement. 

My wife and I started going for long, multiple mile walks when the pandemic set in, which provided the perfect opportunity to test them over long periods of time. 

Lightweight & Breathable 
Close up of Wolf and Shepherd Swiftknit Derby shoes

One of the first things I noticed when I slid on the Swiftknit was how light they are. 

I usually wear leather sneakers or chukka boots while walking, both of which are quite heavy. 

But the mesh upper of the Swiftknits made them extremely lightweight, which made a big difference after the first couple miles, when my feet normally start to get tired. 

The other nice thing about the mesh upper is that it allows for greater breathability, which I didn’t notice when I first started wearing them in March.

But by the time the warm weather rolled around in May, I definitely noticed (and very much appreciated) the fact that these are great shoes to wear without socks.  

Insanely Supportive 

The other big thing I noticed about the Swiftknits was just how nice they were to walk in. 

Wolf Shepherd claims their removable cushioned insole is “like walking on clouds.”

Insoles of Wolf and Shepherd Swiftknit Derby shoes
While I can’t say for sure whether or not it’s comparable to walking on clouds, I can say that the removable, cushioned insole is comfy as hell

As someone who’s only ever walked on earth I guess my perspective is a bit limited, but I’ll be damned if these aren’t the most comfortable shoes I’ve ever worn. 

For years I wore a pair of Nike Air Max trainers when working out, which were incredibly supportive, but not a shoe I would ever wear outside of the gym. 

(I love Jerry Seinfeld’s comedy, but absolutely despise the whole “thick running shoes and jeans” look that he made famous in the 90s.) 

The Swiftkints are honestly just as comfortable as the gym shoes you’d expect from athletic footwear brands like Nike or Adidas.

Side profile of Wolf and Shepherd Swiftknit Derby shoes
The supportive outsole on the Swiftknit is legit, and provides as much comfort as a running shoe

But thanks to the sharp style discussed above, they’re a lot more versatile. 

My wife and I routinely walk to our favorite restaurant, which is about a mile away, and I would always agonize about the shoe choice: 

Do I wear stylish shoes that will look great at the restaurant, but hurt my feet on the walk? 

Or opt for comfort and support on the walk, but feel sheepish (and worse, Seinfeldian) at the restaurant? 

But the Swiftknits basically eliminated that problem for me by perfectly threading the needle between sharp style and supportive comfort. 


The other nice thing about the Swiftknits is that, at $189, the price tag is quite reasonable. 

Those Nike Air Max trainers I mentioned cost between 170 and 200 bucks, and as I say, they can really only be worn at the gym. 

Meanwhile, a stylish pair of casual shoes from a good brand like Beckett Simonon or Allen Edmonds, which could replace the style (but definitely not the support) of the SwiftKnits, would start around $150. 

But by combining the best aspects of both shoes, the Swiftknits basically save you from having to own two separate pairs.

They provide twice as much value as a pair of shoes that’s similarly priced, but not nearly as versatile. 

Total Score for the SwiftKnit Derby: 4.7/5


After I put the Swiftknits to the test, I tried out two more pairs of W&S shoes: the Crossover Loafer and the Crossover Wingtip. 

Much like the Swiftknits, both shoes were extremely comfortable overall and provided a nice blend of style and support. 

But there were also a few differences, as I explain in more detail below.  

Wolf and Shepherd Loafer Review 

Wolf and Shepherd Crossovder Loafers


While I kind of expected to love the Swiftknits, I have to admit I was a little more skeptical when I first saw the crossover loafers online. 

Combining the outsole of a sneaker with a breathable mesh upper is one thing, but adding it to the Italian-leather upper of a penny loafer seems like it would result in the shoe equivalent of Frankenstein’s monster.  

Man's legs wearing Wolf and Shepherd Crossovder Loafers

But once I got them out of the box, it was immediately clear that the founders of Wolf & Shepherd are no Dr. Frankenstein – and the only thing monstrous about these shoes is how freakishly cool they look. 

(Unlike that analogy, which absolutely deserves to be burned at the stake by angry townspeople.) 

Penny loafers occupy kind of a funny place in the world of men’s shoes. 

Some come with a refined toe shape that makes them just as dapper as dress shoes, while others have a squared off toe that’s inherently more casual, like a moccasin or a boat shoe. 

Wolf & Shepherd could have gone with the latter, and offered a loafer that’s casual, comfortable… and not much else. 

But by adding their all day comfort heel to a sleek and (if I dare say) sexy-looking loafer, they’ve managed to create a shoe that’s both athletic, but sophisticated, and relaxed, but refined. 

Comfort & Quality

As I alluded to above, the Crossover collection boasts the same “all-day comfort” outsole as the Swiftknit, and not surprisingly, feels just as good on your feet. 

Side profile of Wolf and Shepherd Crossovder Loafers

But as someone who has previously put up with all manner of back pain and blisters for the sake of a stylish penny loafer, I appreciated the comfort even more in the crossover loafers than I did in the Swiftknits. 

Having the ability to slide on a pair of shoes and know that you’re not only going to be one of the best-dressed guys in any room, but also one of the most comfortable, is just incredibly empowering. 

(And much less painful than the alternative.) 

Total Score for the Crossover Loafer: 4.5/5

The Crossover Wingtip Review 

Wolf and Shepherd Crossovder Wingtips


W&S has actually discontinued the Crossover Wingtip since I first wrote this review.

But I’ve left the below review in place for the sake of thoroughness, to help give you a broad sense of the brand in general (and to help you avoid making the same color mistake that I did!).

The Crossover Wingtips were third pair of Wolf & Shepherd shoes that I tried, and had the same level of comfort and craftsmanship as the previous two.

But I made a rookie style mistake that affected my enjoyment of them.

The wingtip is available in three colorways:

  1. A honey brown leather and white outsole combo
  2. The same honey brown leather paired with a black outsole 
  3. A black leather option, paired with the white 

I chose the second option, which was a rookie mistake. 

Black and brown is a controversial color pairing in the world of menswear. When done right it can look rugged and refined all at once, but it’s notoriously hard to pull off. 

And, as I learned the hard way, it’s annoyingly difficult to pair with the rest of your wardrobe. 

I found that the combination of a thick black rubber outsole on a brown calfskin leather shoe made for a look that wasn’t quite formal, but not all that casual, either. 

In hindsight, I wish I had opted for either of the other two color options. 

Wolf and Shepherd Crossovder Wingtips in black
In hindsight, I wish I had opted for the black wingtips, which are both fresher and more refined

I chose the brown and white combo for the loafers, so I now know firsthand how sharp that looks, and how easy it is to dress up or down. 

But the one that I really should have chosen is the black and white option. 

Combining slick black leather with the pure white rubber sole is bold because it puts a modern, casual twist on the most classic and refined color combo of all time. 

In hindsight I wish I had realized that before placing my order, but alas, the black and white combo will always be the one that got away. 

Total Score for the Crossover Wingtip: 4.2/5


Are Wolf and Shepherd shoes worth it?  

Wolf and Shepherd Swiftknit Derby shoes

After a few weeks, a few thousand steps and one “Hey, I like your shoes” from the barista at my local coffee shop, I can say that in my personal experience, Wolf & Shepherd’s shoes are definitely worth it. 

These are still relatively early days, so the jury is still out on how they’ll hold up over time. 

But based on the quality I’ve seen so far and all the positive Wolf and Shepherd reviews I found online while doing my initial research, all signs seem to point toward durability. 

The brand really does seem to have struck that all too delicate balance between style, comfort and quality, all while maintaining an extremely reasonable price point. 

All three pairs that I tried were incredibly comfortable, and rivaled the support you’d usually expect from big athletic footwear brands like Nike. 

Wolf and Shepherd Crossover Penny Loafer shoes

But they also have elements of timeless style that you’d expect from dress shoe brands like Beckett Simonon and Allen Edmonds, including a refined toe shape and surprisingly impressive leather quality. 

If you’re going to a wedding or work in a formal office, you may want to opt for a proper dress shoe, which is a little more refined-looking, if a lot less comfortable. 

But for a good hybrid shoe that you can wear anywhere from a business-casual meeting to a long hike on the weekend, W&S is hard to beat. 

I haven’t tried any of their other models yet (they offer a pretty good selection, which includes a slip-on/loafer version of the Swiftknit and a ​pretty great looking pair of winterized hiking boots).

But my experience has been so good that I’ve already got my eye on the Crossover Longwing, which might just be the slickest-looking pair they offer. 

If they look and feel as good as the three pairs I’ve tried so far, it’ll be money well spent. 

Overall Score for Wolf & Shepherd Shoes: 4.5/5

Shop Wolf & Shepherd

Wolf & Shepherd Swiftknit Derby Shoes

If you’re looking for stylish, well made and incredibly comfortable shoes, I definitely recommend picking  up a pair of Wolf & Shepherds.

Check out W&S âž¤

Who owns Wolf and Shepherd?

Wolf and Shepherd is still owned by its founder, former college athlete Justin Schneider, and his wife Hope. 

But people sometimes mistakenly attribute ownership to former NBA player Steve Nash. Nash is a brand ambassador for the company who collaborated with them on their crossover shoe, but he’s not an owner of the company. 

Where are Wolf & Shepherd shoes made?

Leather W&S shoes are hand-sewn in Porto, Portugal, while the SwiftKnits are made in China. All models are designed at the company’s headquarters in Los Angeles. 

Are Wolf and Shepherd shoes goodyear welted?

No, Wolf and Shepherd shoes are not goodyear welted. The shoes are constructed in a manner that’s more similar to athletic shoes or running shoes than traditional leather dress shoes.  

Where to Buy Wolf and Shepherd Shoes has a store locator feature that allows you to find a Wolf & Shepherd retailer near you, but one of the best places to buy them is through the website itself. 

They have a pretty comprehensive sizing guide that makes it easy to find the perfect fit, good customer service with their online chat tool, and offer free shipping and returns within 30 days.

Wolf and Shepherd vs Cole Haan

I’ve tried multiple pairs from both Wolf & Shepherd and Cole Haan, and in my experience Wolf & Shepherd’s are more comfortable.

While Cole Haans are definitely more comfortable than a regular dress shoes, Wolf & Shepherd shoes feel as good as sneakers, which Cole Haan can’t quite compete with.

With that said, Cole Haan shoes tend to have a smaller – and therefore sleeker – outsole.

It doesn’t provide quite as much comfort as W&S, but some might prefer it from a style perspective.

The Recap ↓

Wolf & Shepherd Shoes Review

Dave Bowden

Swiftknit Derby – 4.7/5
Crossover Loafer – 4.5/5
Crossover Wingtip – 4.2/5


After a few weeks, a few thousand steps and one “Hey, I like your shoes” from a stranger, I can say that in my personal experience, Wolf & Shepherd’s shoes are definitely worth it.


More Resources â†“
More Reviews & Men’s Style Advice From Irreverent Gent:
More Wolf and Shepherd Reviews From Around Ye Olde Interwebs:

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.