Finding a great pair of dress shoes is one thing. Finding a great pair of dress shoes that are as comfortable as running shoes is quite another.
So when I heard that Wolf & Shepherd was the brand behind the “most comfortable dress shoes in the world”, I knew I’d have to get myself a pair and put them to the test.
In the detailed review below, I’ll cover everything you need to know about Wolf & Shepherd’s Senna Wingtip dress shoes including:
Wolf & Shepherd Senna Wingtip Brogues
- Made In: Portugal
- Style: Wingtip
- Color: Maple Brown
- Formality: Business Professional
- Upper: Italian Calfskin Leather
- Construction: Blake Welted & Cemented
- Price: $365 USD [Buy From Wolf & Shepherd]
The Presentation & Un-boxing Experience
As with all of my shoe reviews, I like to appreciate the presentation of the shoes and the overall experience of un-boxing them when they arrive. A quick look at the box and I knew that Wolf & Shepherd was not going to disappoint.
My Senna Wingtips came in a sleek box with gold-colored lettering which gives the box itself a simple yet elegant look.
Upon opening the box, I found a two-sided card which read “Welcome to the Wolf Pack” on one side and included details about the shoes themselves on the other. I thought this was a nice touch that gave a sense of community as well as a great first impression of the brand.
Additionally, each shoe came with its own individual shoe bag (see photo below) which definitely added some bonus points in the overall value category.
I was very impressed with how stylish the Senna Wingtips looked when I first tried them on. These shoes have a unique design and the high-quality leather has a natural sheen that gives the shoes an elegant look.
There are also lots of subtle details that combine to give the shoe a bit more character than your average dress shoe.
The vamp of the shoe features classic wingtip stitching (hence the name) and there is nice broguing on various sections of the leather upper.
The Senna Wingtip is a particular style of brogue known as a “blind brogue,” meaning the shoe has perforations on the vamp, quarter, and heel, but does not have a toe medallion like a full brogue.
Shoe Size & Fit
Wolf & Shepherd shoes are known for being particularly comfortable, but in order to appreciate this superior comfort you need to make sure you’re shoes are the correct size.
Fortunately, there is a very useful “Sizing” tool on the Wolf & Shepherd website to help you determine the optimal size and width to order based on the specific style of shoe, as well as several other factors.
After filling out my information, I was recommended a US size 11.5 D which is consistent with most of the dress shoes that I own. Based on my experience, as well as the dozens of reviews that I read, it seems like the Senna Wingtips tend to fit true-to-size, but it’s worth using the interactive tool yourself just in case.
How Comfortable Are These Shoes?
Let me start by saying that these are definitely the most comfortable dress shoes that I’ve ever worn.
I found the shoes to be quite comfortable right out of the box. This was a nice surprise considering the fact that I typically need a good week or so to properly break in a new pair of dress shoes.
The real difference in comfort, however, becomes apparent the first time you wear these shoes for a long day that involves lots of walking and/or hours of standing on your feet.
Typically, I’ll begin to experience some sort discomfort and even feel a bit of pain towards the end of a particularly long day of wearing dress shoes. However, I’ve noticed that my feet have been able to make it throughout the entire day without any issues with the Wolf & Shepherd’s.
Patented Comfort Technology
So, how exactly does Wolf & Shepherd make such comfortable dress shoes when it seems like so many others cannot? Much of their success lies in the patented technology and design elements found in their shoes.
As with all Wolf & Shepherd shoes, the Senna Wingtips feature the company’s patented comfort technology which results in a shoe that is as comfortable as it is fashionable.
These particular shoes also feature a proprietary memory foam footbed lined with ultra-soft sheepskin, for an incredibly comfortable wear. Think of a Tempurpedic mattress for your foot.
On the outside, the shoe has a Phoenix TECH outsole along with a high-density EVA foam heel, both of which add to the overall comfort on the foot.
The Senna Wingtips are also one pound lighter than the average dress shoe thanks to some of the efficient design elements like the lightweight Swiss insole. This definitely helps on those days when you have to run between meetings or need to walk a lot.
Price & Overall Value
Whenever I consider investing in a new pair of dress shoes (or investing in anything for that matter) I want to be sure I am getting great value for my money.
At $365 USD these shoes are not exactly cheap. However, if comfortable is what you’re after then there is no question that the Senna Wingtips offer excellent value.
You can purchase these shoes directly from Wolf & Shepherd’s official website.
Wolf & Shepherd is known for exceptionally comfortable dress shoes and the Senna Wingtips did not disappoint. If you’re looking for a pair of stylish dress shoes that will get you through the long days then you can’t go wrong with Wolf & Shepherd.
I’m looking forward to trying some of the other styles that the brand offers in the near future!
- All Wolf & Shepherd Reviews
- Top 10 Best Men’s Dress Shoes
- Best Business Casual Shoes
- See Bespoke Unit’s Shoe Homepage
"Finally an exceptionally comfortable dress shoe that doesn't sacrifice on style. I couldn't believe how great my feet felt after a full day of wearing these shoes for the first time."Rating: 5.0 ★★★★★