Wolf & Shepherd Review: I Tried Their Most Popular 5 Shoes

When I visited Italy a few years ago, I picked up a really nice looking pair of shoes. 

They were sleek, stylish, and made with incredible leather. 

And they also crippled my feet so that, after a long day of walking, I couldn’t take them off without screaming. 

But, man, I looked good. 

Since those troubled walks around Rome, I’ve learned that fashionable footwear doesn’t need to give you blisters and summon you to crawl into restaurants on your hands and knees. 

The search for stylish shoes that I can easily put in 10+ miles of walking led me to Wolf & Shepherd—a brand with the ethos of a performance company, and with styling that can go toe to toe in a boardroom. 

So what’s it really like walking in Wolf & Shepherd’s shoes?

What Is Wolf & Shepherd?

Wolf & Shepherd makes dress shoes and casual shoes fit for the office, but puts a modern athletic-wear twist on them. 

Through the insole and midsole, there are several layers of cutting edge performance materials designed for better shock absorption, comfort, and breathability.

So while it looks like you’re wearing a classic pair of Italian leather Oxfords, Wolf & Shepherd’s goal is that you feel like you’re wearing a pair of comfortable sneakers.

As someone who regularly struts out for a 5+ mile walk about town, but still wants to maintain a classic style, I’ve had enough uncomfortable shoe experiences to get behind this mission. 

Things to Consider Before Buying

Some of Wolf & Shepherd’s shoes, like the SwiftKnit Derby, aren’t at all like the classic derby shoes worn around offices ten years ago. 

With modern office dress-codes steering toward more relaxed styles, I see office workers in the city dressing in what I call “golf-ready” clothes. That’s how I’d define Wolf & Shepherd’s newest lines of shoes—they’re a blend between sleek and performance oriented.

They’re not nearly as chunky as the tennis shoes of yore, but they’re a far cry from what you’d imagine a stock trader in the 1990’s wearing. 

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Still, Wolf & Shepherd does offer a few “classic” styles, like their Closer Cap Toe Oxford or Senna Wing Tip, though they’re phasing these out (so if you like these styles, jump on them while you still can). 

My Hands-On Review

SwiftKnit Derby

Wolf & Shepherd calls this shoe a derby, though it’s vastly different from derby’s of the past. It’s the kind of “dress” shoe you’d imagine the Jetson’s wearing. 

While the world of office footwear has always been dominated by leather, the SwiftKnit Derby hardly has any leather on it at all, save for the pull tabs, footbed, and lacing bridge. 

I like the idea behind the shoe—a totally reimagined office icon. Though it’s definitely a sneaker more than a derby. And it’s a comfortable sneaker, too. 

The upper is made with recycled polyester and is knitted in “zones” that allow greater breathability in certain areas, and more flexibility in others. 

While the SwiftKnit does feature laces, I was pleasantly surprised that you don’t really even need to use them. The sneaker slips on and off quite easily, though you can pull the laces tight for a more snug fit. 

My biggest concern with the SwiftKnit Derby was with the opening you slip your foot into (and that rests around your ankle). Was it going to be too difficult to slip my foot in? Would there be too much room and make it look floppy and uncouth around my ankles? 

It hits the perfect balance: easy to pop on and off, while still staying secure around my ankle so I don’t look like I’m wearing a raggedy old sock. 

The heat has been rising here in North Carolina as spring gives way to summer, and I’ve been loving the breathability of the SwiftKnit fabric. I typically walk from my home to the office (about 20 minutes), office to gym (another 20 minutes), and then gym to home (a final 20 minutes). 

With at least an hour of walking a day, you can imagine that the southern heat and humidity can make a man’s feet a tad sweaty. While the SwiftKnit fabric can’t stop my feet from heating up, there is a decent amount of airflow (certainly way more than my all leather boots), and it make the experience so much more comfortable.

And that’s not even taking into account the sole combination. 

The SwiftKnit Derby features Wolf & Shepherd’s proprietary FloatFoam memory foam footbed, which offers extra padding in the heel and contours nicely around the sides of my foot. The midsole is made with a high density TPU foam, and it’s quite thick at about an inch and a half at the arch of your foot. With that, there’s hardly any shock at all when you take a step.

And on the outsole, W & S has added an abrasion-resistant thermal plastic insert, which should help a lot with durability. 

The heel shape is unique in Wolf & Shepherd’s newest lines, and I’m curious to see how well angular design holds up over a year or two of wear. 

Usually, after so many miles, a foam outsole will wear down considerably. Though in the first 20 miles I’ve worn my SwiftKnit Derby’s, I’m confident the hardened thermal plastic outsole is a boost in the durability department. 

Monaco Loafer

After trying Wolf & Shepherd’s more futuristic derby hybrid, I also was keen to test something a little more “classic” looking. So I picked up the Monaco Loafer in Cognac.

The name is totally fitting—this loafer has such a relaxed vibe, so it makes sense that it’s named after a country that doesn’t even care if you know it’s a country. 

Made with unlined Italian suede, these are super breathable and ideal for warm spring and summer days. The lack of a lining does rule these loafers out for the cooler months, though I’ve never been a fan of loafers in winter anyway. That’s boot season. 

The shape is very sleek and leaves a lot of room at the toe. This definitely helps elongate your feet and works to your advantage if you’re wearing trousers with a tailored fit. 

I was initially a bit confused about the heel of the Monaco Loafer—it’s loose and unshaped. But that’s because you can actually wear these loafers as slippers, too. Just fold the heel down and now you’ve got a fancy pair of suede slippers. 

The Monaco Loafer features the same FloatForm insole and footbed as the SwiftKnit Derby, which is a bit shocking because it still keeps such a low profile. 

In the intro, I mentioned getting a pair of Italian shoes that absolutely destroyed my feet. But I was glad to wear them because they looked good. The Monaco Loafer is the shoes I wish I had then, because it looks classy and stylish, and is way more comfortable. 

Crossover Victory Trainer

The Crossover Victory Trainer is Wolf and Shepherd’s flagship shoe, meant to blur the line between work and leisure. 

This hybrid trainer looks like it was worn by a vintage Italian racecar driver, only with modern updates that would allow you to dominate the squash court. And with the amount of Italian leather on these, it seems to fit that race car driver profile well.

The trend of “athleisure” apparel and footwear has grown by leaps and bounds in the last few years, but Wolf and Shepherd has a slightly different angle with this shoe. Meant to provide athletic performance and comfort in the office and business space, it seems more appropriate to create a new footwear category.

“Athbusiness”, perhaps?

Doesn’t quite have a ring to it.

The idea of achieving athletic performance in the office space brings back memories of the “Parkour” cold open from The Office, but I’m sure that’s not what Wolf and Shepherd had in mind for these trainers. 

In their own words, the Crossover Victory Trainer is, “Made for winning.” Featuring full-grain Italian calfskin trim, foam-injected scuba lining, and a high-density TPU sole, I can confirm that it’s hard to not feel like a winner while wearing these. 

The uppers’ calfskin trim is complemented by breathable sport mesh uppers, so you get the formality of calfskin leather and the aeration of a running shoe. I’m a big fan of this combination, especially when combined with the TPU performance sole. 

Take it from the greatest NFL receiver of all time, Jerry Rice: “If you look good, you’re going to play well.” 

Rice is well-known for his elaborate and particular dressing routine before games, and he attributes much of his success to the confidence gained by feeling his appearance is top-notch.

I get the same sense while wearing Wolf and Shepherd’s Crossover Victory Trainers. The combination of physical style and performance affects my mental confidence and performance for the better.

The insoles feature a memory foam footbed covered by soft sheepskin. The memory foam contoured to my foot almost immediately and made these comfortable from the first step. There was no noticeable break-in period, but the shoes get more comfortable as you stretch out the TPU sole. 

I’ve done a good bit of running in my day and other sports that require adaptive, responsive footwear, like tennis and racquetball. The sole on these trainers is thick and offers great shock-absorption, but is also light enough to keep me light on my toes and fast.

This shoe really is the marriage of casual dress shoe and athletic performance sneaker, and is streamlined by the luxury details to make a cohesive product.

This TPU sole also comes equipped with a high-traction, thermal rubber outsole which I found to give great grip in all environments. It also serves to protect the TPU sole from wear and tear, as the hard rubber can take a beating without wearing down quickly.

The fact that these shoes are called “trainers” was initially confusing to me, as the brand language describes these as shoes for the office and business meetings, but features photos of guys wearing these in sweat suits. 

They’re meant for both, which I confirmed by going to the gym and hitting a hard leg day without foot discomfort.

While these trainers command a hefty price tag of $269, I think they’re perfect for the modern office and business environment, which prioritizes efficiency and productivity over formality. 

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Pair these with chinos or dark-wash jeans and a polo and you’re ready to crush the game. I think Wolf and Shepherd has recognized that much of business is conducted outside the office these days, and the Crossover Trainers are perfect for these more casual environments.

These shoes come in standard D width and have half-sizes, so it shouldn’t be difficult to get the size that works best for you. These fit true to size for me, so I recommend ordering your usual sneaker size.

SwiftKnit Loafer

Featuring a similar sole to the Crossover Victory Trainers, the SwiftKnit Loafer steps it down a notch in terms of formality, but steps it up in comfort. 

These loafers are perfect for summer happy hours with work and friends alike, and will leave you comfortable for hours on your feet when there inevitably isn’t enough seating. 

I grabbed a pair of their Coast/Coast colorway, which seemed applicable for a number of summer outfits, especially if you’re going for that Miami beach style. 

The SwiftKnit Loafers feature a recycled polyester upper, which has “zoned” knitting to provide stability and support where it’s needed. This zoned knitting describes portions of the upper that have denser knitting, resulting in a stiffer fabric. 

The dense portions provide support, while the lighter portions provide ample breathability.

I was slightly worried that the opening would be either too snug or too loose. I’ve had loafers that are a bit too loose and flop around on my feet unceremoniously, and I’ve also had loafers that squeeze my feet like a tourniquet. 

Although the opening to the SwifKnit Loafers looks fairly long, I found it was a perfect fit: not too snug, not too loose. 

The zoned knitting seems to help with getting this perfect fit, as the less dense zones are more elastic and stretch nicely around the foot without being constrictive. 

Slipping these loafers on was a breeze, especially with the premium leather pull-tabs. 

The sole of these loafers differ slightly from the Crossover Victory Trainers, primarily in the heel-toe offset. This offset describes the difference in thickness between the heel of the sole and the forefoot, and in the loafer goes from 15mm in the heel to 5mm at the front.

This is a 10mm offset, which is the same as my current pair of running shoes. In terms of heel-toe offsets this is fairly large, and gives the feeling with each step like your foot is rolling forward from your heel to your toe. I find it to be exceptionally comfortable, and love that they included it in the design of these loafers.

The sole features the same thermal rubber outsole for traction and protection of the TPU sole, which is another design feature I like. Most loafers I’ve worn don’t seem to have ever heard of “traction” or “anti-slip” features, but the SwiftKnit Loafers offer just as much grip as the Crossover Trainers. 

I wouldn’t wear these in the office, perhaps with the exception of Casual Friday, but they’re great for casual outings or everyday wear outside of the office, especially in the summer. 

Regarding sizing, I found that these fit slightly large. Wolf and Shepherd recommends ordering a half size down for all slip-ons, which is a bit odd to me given that the SwiftKnit Loafers don’t come in half sizes. 

I still recommend ordering true to your sneaker size. Even with the shoes being slightly long, the fit is still snug enough around the heel and ankle to make these comfortable. 

The SwiftKnits feature a removable memory foam footbed, lined with their signature soft sheepskin. This is a useful feature because Wolf & Shepherd offers both wide and narrow footbeds that can be swapped into the SwiftKnit for a more comfortable fit. 

Also, if the footbed wears down before the outsole and sole, which is likely, you can snag a new footbed and feel like you’ve got a new pair of loafers again.

I like the versatility these loafers provide for summer outfits. Whether it’s dinner and drinks or a food truck festival, I can pair these with chinos, shorts, or slacks and be dressed to impress in comfort.

Once again, these come with a hefty price tag of $179, but the style and benefits justify the cost for me. 

Crossover Golf

The Crossover Golf is Wolf & Shepherd’s first sport-forward shoe, meaning it’s meant exclusively for golf and not for the office. 

The Crossover Golfs continue Wolf & Shepherd’s use of Italian leather, this time with a water-resistant variety that covers much more of the upper than the Crossover Trainers. I appreciate this, as many golf outings require waking up at an unholy hour and trudging through dew-soaked grass.

Nothing better than starting 18 holes with wet socks. 

The water-resistant Italian leather effectively keeps water out and my socks dry, and is paired with the same breathable, recycled mesh uppers as seen in the Crossover Trainers. 

I’m glad the entire shoe isn’t this water resistant leather, given that this leather’s ability to keep water out also happens to be good at keeping moisture in. That’s a rough time if you have sweaty feet.

To help aerate even further, the Crossover Golf’s have breathable vents in the forefoot. 

These shoes also feature a waterproof rubber mudguard around the toe that helps keep the worst of the elements from messing up your leather uppers. 

Like Wolf & Shepherd’s other shoes, the Crossover Golf features a TPU sole, but this time with a heel counter that helps give stability and control. This heel counter is just an extra portion of TPU sole that sticks slightly out of the back to place more weight in your heels. 

This helps you maintain your balance when you’re in the rough, at the edge of a pond. 

As you’d expect, the thermal rubber outsole we saw on Wolf & Shepherd’s other shoes was traded out for something with extra grip and traction. Their proprietary CrateTech rubber grip outsole is designed for full-course traction, rain or shine. 

I don’t play golf frequently, but I know for a fact that my game would have improved with the proper footwear. These offered the stability, support, and traction I was looking for in a few practice swings.

I also like that the CrateTech doesn’t take away from the shoe’s sleek profile. Despite having some massive grooves and grip on the outsole, it’s not very noticeable from the side. The hard rubber also gives nicely on pavement and hard flooring, so you can walk seamlessly between the fairway and clubhouse.

The Crossover Golf also includes a memory foam footbed with sheepskin cover, which proved immensely comfortable in Wolf & Shepherd’s other shoes and is the same here. 

The interior differs slightly, in that the Crossover Golf has a padded neoprene lining. I’m a big fan of neoprene interiors, as there’s little to no chance of getting a blister or chafing with these. 

These shoes fit true to size, and I recommend you once again order your true sneaker size for the best fit. Half-sizing is available, but Wolf & Shepherd’s website is unclear whether or not the Crossover Golf has the removable footbed and alternate width footbed replacements.

The Crossover Golf being the brand’s first sport forward shoe seems smart to me. With golf courses being a regular setting for business and networking events, if you’re already a Wolf & Shepherd fan and don’t want to leave their comfort for the golf course, now you don’t have to. 

The shoe had a small break-in period for me, likely due to the CrateTech outsole. That being said, the neoprene lining and memory foam footbed are so comfortable I barely noticed the stiff outsole, and it loosened up after about 2 solid outings.

What do Other Reviewers Say About Wolf & Shepherd? 

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With over 4,000 reviews on the Wolf & Shepherd site, I had a lot of data to pore over. Comfort came up in nearly every review. Some folks say these are the most comfortable shoes they’ve ever worn, even when compared to regular sneakers. 

One downside I saw multiple times was on sizing: many reviewers said their Wolf & Shepherd’s fit a bit on the large side. Some models don’t come in half-sizes either, so in certain cases it was impossible to get the perfect fit. 

We ordered our true size for all the models we got and we found the fit to be on-point.

Our Thoughts Overall

FAQs