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Fit & Sizing Every time my dad and I hang out, we play golf. It’s his favorite thing.
Me? Not so much.
But since he’s coming out for a few week visit, I needed a new pair of shoes that fit the “golf dress code,” and I was tired of wearing his old beat up shoes for walking on the green.
So I picked up a pair of the Wolf & Shepherd Longwing Crossover Oxford sneakers.
Are they any good? Here’s what I thought.
Table of Contents
Wolf & Shepherd Crossover Longwing Overview
The Wolf & Shepherd Crossover Longwing is an Oxford shoe. It’s also a running shoe.
What?!
Wolf & Shepherd has fully leaned into the blurred lines of office formal and business casual. While the upper of this shoe has all the hallmarks of a dressy Oxford (closed laces, rich leather with a shine to it), the insole and outsole are built like a pair of running sneakers.
I guess someone was bound to blend the two.
I can see this shoe being perfect if your go-to style is business casual and you rock a lot of polos and chinos. The shoes aren’t your basic sneakers—they’re a bit elevated. But you’re certainly not sacrificing comfort.
Things to Consider Before Buying the Wolf & Shepherd Crossover Longwing
While there are elements of an Oxford dress shoe in the design, the Crossover Longwing definitely isn’t a dress shoe.
I say this because I see a lot of guys who wear these kinds of sneakers like they’re actual formal shoes. I don’t recommend this Crossover style for anything formal. It’s a casual shoe, all the way.
Once you understand that aspect, all that’s left is to choose the leather you want. At the time of writing, there are five different leather options: three calfskin, and two suede choices.
The pics you see of my shoes are with the Maple calfskin leather.
With the upper of an Oxford dress shoe and the sole of a golf shoe, the Wolf & Shepherd isn’t like any other sneaker I’ve seen. It’s easily the most comfortable Oxford I’ve ever worn, but it’s not cut out for any formal or even semi-formal occasion---this is a nice sneaker, but it’s as casual as they come.
Wolf & Shepherd Crossover Longwing Review
First Impression
I was pretty surprised when opening up the box to check out my new Wolf & Shepherd Crossover Longwings. If you didn’t see the sole, you wouldn’t be able to distinguish them from some of the nicer dress shoes on the market.
As I mentioned, I got the Maple color, which is a deep rich brown. I’ll discuss the quality of the leather a little later, but from a style-perspective, I think this is the most versatile option.
Deep brown goes with pretty much everything (though the light grey suede was my second choice).
I think the Crossover Longwing is the very definition of business casual.
In terms of what to wear with the Longwing, I’ve been wearing mine with chinos and a polo. To me, that’s the best mix of casual style that also looks like you put in a bit of effort.
Leather Quality and Care
There’s not many calfskin leather sneakers out there. Usually brands opt for the cheaper stuff, but Wolf & Shepherd is bringing the good stuff.
I really like that there’s a bit of shine to the leather. The upper is basically what I’d expect from a dress shoe at this same price.
Because it’s calfskin, the grain pattern is tight. This means that the leather creases and breaks in more gently compared to other leathers with looser grain structures. For you, that means these sneakers will stay relatively “new” looking for longer.
There’s a breathable fabric lining on the inside of the shoe, which is designed for sweat wicking and keeping your feet dry. I’m not always a huge fan of fabric linings because they tend to wear out much faster than leather, but I haven’t had any issues with this lining.
The leather doesn’t need much care, but you could use any matching polish on the leather to bring the shine back. For conditioning, I’ll use Venetian Leather Balm because it brings that shine back and nourishes the leather well.
Ventian is our favorite leather conditioner. It provides supreme conditioning, slight weather resistance and works on a wide range of leathers without darkening. It's one of the priciest options, but you really can't go wrong with it.
Don’t use any waterproofing sprays on these shoes—they’re not storm shoes, but if they get wet, it shouldn’t be too big of a deal.
Sole
The sole is the fun part of this sneaker. The insole is removable, so you can add your own custom insert if you need more arch support.
But if you want to keep the insole in (which I do), here’s what you need to know: it has a leather footbed, the foam is high density, and there’s additional padding in the heel, which I really like.
Below the removable insole is a fiberboard—definitely avoid soaking these shoes through (i.e. don’t go in the lake after your golf ball).
And the outsole is a two piece rubber outfit: the white rubber is soft and offers a lot of shock absorption, and the black is more firm and durable.
I really like the way they did the sole—it’s not so cushy that you feel like your ankles are going to twist, but it’s got enough give to make these shoes really comfortable.
With the upper of an Oxford dress shoe and the sole of a golf shoe, the Wolf & Shepherd isn’t like any other sneaker I’ve seen. It’s easily the most comfortable Oxford I’ve ever worn, but it’s not cut out for any formal or even semi-formal occasion---this is a nice sneaker, but it’s as casual as they come.
Fit and Sizing
I picked up my true size (10.5), which is what I normally get for dress shoes and sneakers, and these fit perfectly.
At the moment, Wolf & Shepherd doesn’t have any wide sizes available for the Crossover Longwing, so if you’re an E-width or wider on the Brannock device, you may want to size up a half-step.
But very few sneaker companies offer wide sizes anyway, so you should be good to go getting whatever size you normally opt for.
Break-in Period
There’s basically no break in period with these shoes. The leather will break in and stretch a tad as you wear them, but they’re immediately comfortable.
I was able to walk several miles right away in my Crossover Longwings without needing to switch them out.
What do Other Reviewers Say?
The Crossover Longwing is one of Wolf & Shepherd’s most popular shoes and has over 1,000 reviews.
The positive comments cover the whole gamut: comfort, style, durability. These get a 4.9-star rating out of five, so most reviewers are happy with what they got.
Most of the times people took a star off their review, it was because of the lack of variety in widths. So if you have larger, wider feet, you may have to try a bigger shoe than normal and add an insert.
My Thoughts Overall On the Wolf & Shepherd Crossover Longwing
What I Like
- It’s the most comfortable Oxford I’ve worn.
- The dark maple leather is rich and has a nice shine to it.
- I like that the insole is removable so I can add an orthotic if I feel I need extra arch support, though the insole currently in it does a good job in that area already.
What I Don’t Like
- The style is a bit outside what I normally wear—it’s definitely a business-casual shoe for the golf-crowd. .
Who is the Wolf & Shepherd Crossover Longwing for?
If your go-to outfit is a pair of chinos and a polo, you do a lot of walking, but you want a sneaker that at least looks a little classy, then the Wolf & Shepherd Crossover Longwing is the way to go.
The Verdict
The Wolf & Shepherd Crossover Longwing is a great everyday shoe—it’s comfortable and it has the durability you’d want if you put in a lot of walking miles.
From a style perspective, it’s not my favorite—just because what I’d call “New American Business Casual” style isn’t what I normally go for.
Or you could call it Golf Business Casual.
If that’s your style, then I think these sneakers are awesome. For me, I like my sneakers to be sneakers and my dress shoes to be dress shoes.
From a quality, comfort, and durability perspective though, the Crossover Longwing is great, and I think the price is fair.
With the upper of an Oxford dress shoe and the sole of a golf shoe, the Wolf & Shepherd isn’t like any other sneaker I’ve seen. It’s easily the most comfortable Oxford I’ve ever worn, but it’s not cut out for any formal or even semi-formal occasion---this is a nice sneaker, but it’s as casual as they come.
FAQs
Do Wolf & Shepherd shoes run true to size?
Yes, my Crossover Longwing Wolf & Shepherd shoes run true to size. Whatever size you’d normally get in sneakers or dress shoes is perfect for Wolf & Shepherd shoes.
Can you wear Wolf & Shepherd with a suit?
You can definitely wear the Wolf & Shepherd Crossover Longwing with a suit, but it makes the suit more casual. I wouldn’t wear these shoes to a funeral or a wedding (unless those were casual events). But sometimes a suit counts as business casual depending on how you style it.
Are Wolf & Shepherd shoes made in the USA?
No, Wolf & Shepherd shoes are made in Portugal.
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