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2024 Review: Wolf and Shepherd’s Longwing Crossover Hybrid Dress Sneakers Are Singularly Striking (and Super-Comfortable)

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This 2023 review of Wolf and Shepherd explores the comfortable and extraordinarily unique Longwing Crossover shoe (aka dress sneaker). See why I think these hybrid dress shoes are a conversation-starter for business casual and smart-casual situations (and working from home walks).

Introducing the Hybrid Dress Sneaker

What is a hybrid dress sneaker? In what situations would I actually wear them? Do I really need a pair?

These were some of the questions I asked myself when I set eyes on Wolf and Shepherd’s unique hybrid crossover dress sneaker for the first time way back in 2020 as the pandemic was setting in.

Below I set out to answer those questions and explore why I think these hybrid dress shoes are unlike anything else on the market (and might deserve a place in your stylish business casual wardrobe).

Before I dive in, a disclosure: Wolf and Shepherd provided a pair of Longwing Crossover hybrid dress sneakers to me at no cost for the purpose of a review.

Wolf and Shepherd Coupon: Save 20%

The last time I checked, when I navigated to Wolf and Shepherd’s website, I encountered a pop up offering a 20% discount coupon off of your first Wolf and Shepherd purchase. (Let me know if it worked for you.)

What is a Crossover or Hybrid Dress Sneaker?

Also known as a crossover shoe, a hybrid dress sneaker is a relatively new category of footwear that combines the formal look and design of a dress shoe with comfortable and relaxed sneaker components.

Hybrid dress sneakers are designed to cross over between office and everyday situations, and to occupy the space between a dress shoe and sneaker.

Which companies make crossover or hybrid dress sneakers?

Wolf and Shepherd’s Longwing Crossover is one of the best examples of a hybrid dress sneaker on the market today.

While Wolf and Shepherd has been a pionner in this space, the hybrid dress sneaker category has caught on, and a number of other companies now offer the new footwear style for men. Brands like Wolf and Shepherd include Cole Haan, whose ØriginalGrand and Generation ZERØGRAND lines incorporate elements of a dress shoe upper and rubber sneaker soles, as well as Ace Marks, Allen Edmonds and luxury menswear labels Berluti and Tom Ford.

Sustainable fashion startup Allbirds makes what might be best described as hybrid casual shoes for women and men, featuring a thick sneaker sole and an interesting, casual shoe-like wool upper.

How much do Wolf and Shepherd’s Longwing Crossover hybrid dress sneakers cost?

Last I checked, the Longwing Crossover hybrid dress shoes cost $289, according to Wolf and Shepherd’s website.

About Wolf and Shepherd

Wolf and Shepherd is a men’s lifestyle and fashion brand specializing in uniquely comfortable and versatile dress shoes for men. The company is a great example of the kinds of innovative, direct-to-consumer brands helping men dress sharp in the digital age.

Entrepreneur Justin Schneider founded Wolf and Shepherd in 2015 initially with the goal of creating the world’s most comfortable dress shoe.

Photo courtesy of Wolf and Shepherd

Justin, pictured here with his wife and business colleague Hope holding the Longwing Crossover, began his journey a year earlier, experimenting by cutting up and manually gluing together dress shoe uppers and sneaker soles.

Those initial efforts led Justin to develop a working prototype of a dress shoe featuring an innovative foam sole.

From there, he identified a factory in Portugal and an Italian leather supplier, and perfected a proprietary, patent-protected foam.

I’ve had a chance to review Wolf and Shepherd’s Closer Cap-Toe Lace-up Oxfords and Bannister Derby dress shoes.

In my review of those cap-toe oxfords, I wrote that,

They’re lightweight…and boast a bevvy of technologies in their multiple insole layers from high-density foam heel adapted from athletic shoes to carbon-fiber arch support and sheepskin lining in the upper-most layer.

All of that technology is housed in a pair of shoes that look professional and sleek with just a little bit of flair.

I have put that pair of Closer Cap-Toe Lace-Ups through the wringer over the past two years, and they remain in good shape and continue to feel great.

Justin told me in an April 2020 interview that, “we initially thought that our dress shoes would be for an older guy, but what we found from our customer data is that [a typical customer] is the 25-35 year old guy needs to impress.”

Those comfortable dress shoes, Justin observed, are a “a need product.”

Guys need a comfortable dress shoe for work, for weddings, and for Aunt Ida’s 80th birthday party.

From dress shoes to business casual: Hybrid Longwings and Swiftknit Derbies

While Wolf and Shepherd used to be an awesome option for dress shoes for men, the company has completely transitioned out of traditional dress shoes to focus on business casual and hybrid footwear like the Crossover Longwing dress sneaker and Swiftknit Derby.

The COVID-19 pandemic accelerated a transition to business casual and smart casual footwear, and Wolf and Shepherd decided to double-down on the trend, leaving me searching for a new favorite option for comfortable dress shoes.

First impressions of the Longwing Crossover hybrid dress shoe

When it first launched, Wolf and Shepherd focused primarily on producing extremely comfortable dress shoes with hidden sneaker technology (along with attractive Gunner Driver moccasins and low-top Glider leather sneakers).

While the company incorporated performance elements of a sneaker into its dress shoes, it did so discreetly. Wolf and Shepherd’s original dress shoes still looked very much like dress shoes.

The Longwing Crossover shoe is a completely different animal.

So different, in fact, that it is carving out a new category of footwear: the hybrid dress sneaker.

I’m tempted to say you either love them or you hate them, but it’s probably more accurate to say that you can’t look away.

At least I couldn’t.

Upon seeing them for the first time, I thought that this crossover shoe was singularly striking and like nothing I’ve ever seen before.

That’s not to say that it was love at first sight.

To be honest, I wasn’t sure I needed them.

And I wasn’t sure in which situations I would wear them.

And that thick, distinctive heel is, well, pretty thick and distinctive to be paired with a dress shoe upper.

But I kept thinking about them.

And they grew on me.

As they grew on me, I saw opportunities to deploy them. At receptions in Georgetown. On Saturday night date night. Potentially even at work when I don’t have client meetings.

By the time Wolf and Shepherd sent over a pair, I was ready to try them out.

Unboxing the Longwing Crossover Shoe

The Crossover is just as striking when you take it out of the box as when you see it online.

Under the hood, it contains the same kind of technology that makes all of Wolf and Shepherd’s shoes special, like a full-grain Italian calfskin leather upper treated with a proprietary coating to improve softness and longevity.

The footbed features memory foam, and the outer sole is constructed of high-density thermoplastic polyurethane (TPU), a lightweight material designed to resist splitting and scuffs.

There were a couple of light scuffs on the right toe of the leather upper but, otherwise, the shoes were in pristine shape.

Taking them out of the box, they weren’t heavy, but they aren’t exactly ultra-lightweight sneakers either.

How much do Wolf and Shepherd’s Longwing Crossover shoes weigh?

Each of the crossovers weigh approximately 19 ounces.

As a reader pointed out in the comments below, this makes the Longwing Crossovers slightly heavier than your typical shoe or sneaker.

By comparison, my Beckett Simonon Morgan sneakers weigh 14.5 ounces each, and my dress shoes from Ace Marks and Paul Evans both weigh approximately 14 ounces each.

If you’re looking for a lighter crossover from Wolf and Shepherd, their SwiftKnit Derbies weigh just 11 ounces each and are a great option for a minimalist knit sneaker.

If you’re looking for a lighter weight dress sneaker, Modern Fellows’ guide to the Best Dress Sneakers for Men for Every Budget has dozens of other options.

Wolf and Shepherd x Steve Nash (WSXSN)

Flipping the shoe over, the bottoms of the Crossover’s soles are emblazoned with WSXSN, which stands for “Wolf and Shepherd with Steve Nash.”

That would be eight-time NBA All-Star, two-time MVP and Hall-of-Famer Steve Nash, who collaborated with Wolf and Shepherd on the hybrid dress sneaker.

Inside the shoebox is a note from founder Justin Schneider, who writes of the collaboration that,

Working with Steve Nash on this shoe has been a uniquely fun, inspiring project for us all. Together we had an idea to create something that blended athletic ingenuity, work functionality and everyday-wear appeal in a way that hadn’t been done before.

Wolf and Shepherd donates 13% of the sales of the Longwing Crossover directly to the Steve Nash Foundation. Registered in the United States and Canada, the Foundation works to assist children in underserved communities with health, personal development, education and enjoyment of life.

Reviewing Wolf and Shepherd’s Crossover Dress Sneakers in Real Life

Stepping into the Crossovers for the first time, I felt the cushioned memory foam under my feet and noticed the high sole, which adds a little lift to my 5’8” frame.

Unlike traditional dress shoes, which start out stiff and soften after wearing, these hybrid dress shoes feel soft and immediately comfortable thanks to the pre-treated leather and sneaker sole.

That’s not to say that they don’t require any breaking in. The leather still needs some time to soften up some more, and your feet need some time getting to know the memory foam.

I made the mistake of immediately lacing up my Crossovers for a long walk around the neighborhood. My feet weren’t used to the memory foam, and my calves were a little sore that night.

After that episode, I broke them in gradually for a couple of days, wearing them around the house and my yard for short periods, which helped them adjust to my feet and vice-versa.

Now the shoes feel great throughout my days of working from home during the COVID19 crisis, including on long daily walks around the neighborhood.

I’ve been wearing the cross-overs with jeans and a t-shirt with my kids, as well as with chinos and a button down shirt.

They are a welcome addition to my smart-casual wardrobe, and a unique change-of-pace alongside other options like Chelsea boots and work boots for when dress shoes are too dressy but sneakers too casual.

One note on fit: the website suggests ordering a size up from “your Wolf and Shepherd dress shoes,” but I fit right into my normal size 9.

Like the socks? They’re from Unsimply Stitched.

Dress Sneakers are Definitely a “Want” Product

“The crossover is a want product,” observed Justin. “It’s highly versatile, but it’s also generic-looking so you can wear it with anything.”

Justin told me that he’s seen substantial demand for these hybrid dress shoes, which has been transformative for Wolf and Shepherd.

“The customer response, the page visits, the click-throughs started to create a flywheel for us,” he said, noting that the turn on the Longwing Crossovers is four times greater than their previously-best selling items.

Justin added that the order frequency is higher because customers know they can wear it in far more situations than a typical dress shoe.

Next up: Crossover Hybrid Dress Sneaker Wingtips and Penny Loafers

Given the success of the Longwing, it’s not a huge surprise that Wolf and Shepherd is expanding their line of crossover sneakers.

In the months to come, Wolf and Shepherd will introduce a black wingtip hybrid dress shoe featuring soft, Italian calfskin. In addition, the company will release a hybrid penny loafer.

At the end of summer 2020, Wolf and Shepherd released a long-awaited hybrid dress shoe-slash-sneaker, the SwiftKnit Derby, featuring a single-thread zoned knit upper. It’s the company’s most casual hybrid shoe yet, and is extremely lightweight and comfortable. (See my review of Wolf and Shepherd’s SwiftKnit Derby for more details.)

As for me, it’s clear I don’t need a pair of hybrid dress shoes.

Working here in Washington, DC, it’s definitely not the kind of shoe that I would wear to a meeting with a Member of Congress or to the White House, though these days. And I sure don’t need a pair to kick around a soccer ball at the park on the weekend.

But do I want a pair?


About Jake

Jake is an expert on men’s style and fashion based in Washington, DC. He founded Modern Fellows in 2012 to get to know the entrepreneurs and innovative clothing and lifestyle brands helping men dress sharp in the digital age. He has published hundreds of articles on style and apparel, and regularly interviews small business CEOs and startup founders about industry trends. Jake has written about entrepreneurship, international business and fashion for outlets including Business Week, Forbes, Inc., Details Style Syndicate and Primer Magazine.

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3 thoughts on “2024 Review: Wolf and Shepherd’s Longwing Crossover Hybrid Dress Sneakers Are Singularly Striking (and Super-Comfortable)”

  1. twice as heavy??? sounds like you buy ultra-lights sneakers and dress shoes…why would you even be interested in this shoe? This shoe is for someone that needs a dress shoe and needs the comfort of a dense foam sole, the last thing i’m looking at is weight. Not to mention the review that you are posting to mentions specifically the weight of the shoe. Seriously???

  2. These Crossover Longwings are heavier then any chelsea boot I own, twice as heavy as any dress shoe I have owned and 2.5x as heavy as any sneaker I own. The shoe feels clunky on the foor and do not flex to even the smallest degree. I have been manipulated by marketing once again. This shoe combines the worst most undesirable qualities from sneakers and dress shoes then fools you into buying them by promoting the 2×4 wood plank of a shoe with pictures of basketballs Legend Steve Nash running and jumping with them on. What a MAJOR LET DOWN. My 1st experience with this company will be the last. If you like this shoe I mean no disrespect and you must have very strong durable feet. I bet you look supa fly in them but probably at the cost of needing surgery at a later point.

    • Hi William, Thanks for your comment and for sharing your experience. You’re right that the Longwing Crossovers are heavier than some other sneakers and shoes out there. The Longwing Crossovers weigh 19 ounces each. By comparison, my Beckett Simonon Morgan sneakers weigh 14.5 ounces each, and my dress shoes from Ace Marks and Paul Evans both weigh approximately 14 ounces each. If you’re looking for a lighter crossover from Wolf and Shepherd, their Swift Knit Derbies weigh just 11 ounces each. The extra couple of ounces haven’t been an issue for me. When they’re on my feet, the Longwing Crossovers don’t feel heavy. Then again, I don’t play basketball in them.


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