Deal Alert: These Wolf and Shepherd Dress Shoes Balance Comfort and Style for the New Normal

This post may contain affiliate links. Learn more.

If you are looking for stylish and comfortable dress shoes as you go back to the office, explore this review of Wolf and Shepherd’s Bannister Derby shoes, which are up to 64% off.

Deal Alert: Wolf and Shepherd’s classic dress shoes are on sale

Wolf and Shepherd has put their entire line of classic dress shoes on sale, including the Bannister Derby, Senna Wingtip, and Closer Cap Toe.

These shoes, which used to cost $349, can now be purchased for between $125-$195 on “final sale” terms.

Comfortable dress shoes are essential for the new normal

As we return to offices, comfortable dress shoes are one of the most essential items for the new normal.

While hybrid work schedules and the ability to dress for your day are likely to provide many more opportunities to wear stylish leather sneakers, minimalist wool and knit shoes, and sleek crossover hybrids, there are still times when only dress shoes will do.

Post-pandemic, I’m looking for dress shoes that are versatile and stylish enough to wear with a suit or jeans. And, given how accustomed I have become to wearing sneakers, driving shoes and sandals during the pandemic, those dress shoes need to be extremely comfortable.

Before jumping into this review: Wolf and Shepherd provided a pair of Bannister Derby Shoes in oak for free for the purpose of a review.

Wolf and Shepherd’s Bannister Derby shoes

About Wolf and Shepherd

Wolf and Shepherd began with founder Justin Schneider gluing sneaker insoles to dress shoe uppers in 2014 with the aim of making a more comfortable dress shoe. He ultimately created a prototype of a classic dress shoe with an innovative foam sole.

Justin launched a presale in July 2015 after finding a factory in Portugal who could produce these sneakers-disguised-as-dress-shoes, sourcing leather from a luxury Italian supplier and perfecting a proprietary, patent-protected foam for comfort.

(Runner Juris Silenieks even set a new world record by running the Hotlanta half marathon in Wolf and Shepherd’s comfortable dress shoes.)

From dress shoes to hybrid Crossovers and Swiftknit derbies

While Wolf and Shepherd began by offering traditional looking though much more comfortable dress shoes, Justin told me way back in 2018 that he didn’t want to stop there.

“Ultimately, we want to be more than a go-to shoe for men; we want to be a go-to brand for style, quality and performance,” Justin told me in an interview.

In 2019, Wolf and Shepherd expanded their product line, launching the Longwing Crossover.

The Crossover is a unique hybrid of a dress shoe upper and thick sneaker sole. In my review of Wolf and Shepherd’s Longwing Crossover, I suggested the hybrid was a “conversation-starter for business casual and smart-casual situations.”

In the late summer of 2020, amid the pandemic, Wolf and Shepherd released the SwiftKnit Derby, an even more casual, slip-on shoe that sports a single-thread knit upper and a sock-like feel.

Wolf and Shepherd’s Swiftknit Derbies

(These Swifknits are one example of a growing universe of minimalist knit shoes from brands that also includes Allbirds and Vessi.)

Demand for Wolf and Shepherd’s more casual shoes soared during the COVID-19 pandemic. Justin told me in July 2021 that, “we can’t keep our Crossover or Swifknit lines of products in stock.”

He said that Wolf and Shepherd continues to focus on their Crossover and Swiftknit lines of products given the demand.

The company has added a Crossover penny loafer, Crossover Chukka, Crossover City Hiker boot, several suede versions of their Crossover Longwing, Crossover Wingtips, and an array of limited edition Swiftknit Derby shoes for women as well as men to their product mix.

Fiona Fergusson, Wolf and Shepherd’s Marketing Manager, added that, “there is still a huge shift towards our hybrid styles as many of them, such as the Crossover Wingtip and the Crossover Longwing can be dressed up really well.”

Reviewing Wolf and Shepherd’s Bannister Derby shoes

I have had experience with Wolf and Shepherd’s traditional dress shoes before, having reviewed their Closer Cap Toe lace up oxfords.

Like the Closer Cap Toes, Wolf and Shepherd’s Bannister Derby shoes are exceptionally comfortable, owing to a tremendous amount of cushioning inside.

Wolf and Shepherd’s shoes feature a cushioned footbed, a thickly-padded tongue and HDEVA (ethylene-vinyl acetate) memory foam in the heel.

Also inside is an extremely soft sheepskin lining, and carbon fiber inserts that make their shoes up to 1 pound lighter than other brands.

As for looks, Wolf and Shepherd has executed well on the classic derby style.

I have always liked the look of a derby shoe, which tends to be regarded as a bit more casual than a traditional oxford shoe.

Wolf and Shepherd’s Bannister derbies look sleek and clean without broguing or embellishments that would take the shoe in an even more casual direction.

These shoes can be dressed up with a suit, but I can also wear them with smart jeans. (In the photos in this article, I’m wearing them with one of my favorite pairs of Revtown jeans.)

Finally, the shoes feature a PhoenixTECH outsole that enables them to be resoled in both the forefoot and heel.

Verdict: Get Wolf and Shepherd’s classic dress shoes before they’re gone

Wolf and Shepherd’s original mission, to offer stylish dress shoes that are as comfortable as a sneaker, is even more critical in the new normal.

While the demand for more casual shoes makes it hard to argue with their current focus on its Crossover and Swiftknit lines, Wolf and Shepherd does versatile, stylish and comfortable dress shoes as well as anyone else out there.

I hope they continue to shower some attention on classic dress shoe models.

The company noted that they will be phasing out their current lineup of dress shoes, but that there may be some new designs in the works.

Wolf and Shepherd sale

In the short term, Wolf and Shepherd’s decision to phase out their existing lineup of classics means there are impressive deals to be had on their stylish-yet-comfortable dress shoes:

As mentioned earlier, Wolf and Shepherd has put their whole stock of classic dress shoes on sale. You can get the Bannister Derby, Senna Wingtip, and Closer Cap Toe, which retailed for $349, for between $125-$195. Just remember to read the fine print on their “final sale” terms.

Longer term, Justin assures me that, “we will likely keep a Classics section to shop with key dress shoe styles though as we move forward.”

I hope so, because the world still needs comfortable dress shoes.


About Jake

Jake is passionate about exploring entrepreneurs' global journeys. He founded Modern Fellows in 2012 to get to know the entrepreneurs behind the innovative brands helping men dress sharp in the digital age.  Jake has written about entrepreneurship, international business and/or fashion for outlets including Business Week, Forbes, Inc., Details Style Syndicate and Primer Magazine, and has provided analysis on international business for BBC Radio, NBC News, CNN and Time Magazine.

Other cool stuff:

* For comfortable Athleisure clothing for women and men, try these 25 alternatives to lululemon.
* Find 21 Alternatives to Warby Parker that also let you try on prescription eyeglasses at home.
* The Essential List: These 106 innovative menswear startup brands will transform your wardrobe
* Upgrade your work-from-home wardrobe with comfortable yet professional-looking workleisure clothing made from stretchy performance fabrics.
* Get $50 off your first suit at Black Lapel, one of my favorite online custom tailors.
* Try these impressive digital native brands for your next Zoom shirt. (Because you need a new Zoom shirt.)
* Browse my favorite men's style books.
* Discover the best places to buy unique and colorful socks online.
* Check out these gorgeous, affordable watches with numbers.
* Score $20 off your first shirt at Proper Cloth, one of my favorite online custom shirtmakers.


Innovative Brands in your Inbox

Sign up to discover impressive entrepreneurs and innovative brands.


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.