Crossover Derby

With the refined style to approach the most formal settings combined with the agility to take on the unexpected, there’s nothing quite like the Crossover Derby.
Regular price $195
Sale price $195 Regular price $295
Mens Crossover™ Derby black-black  Calfskin View 39
Mens Crossover™ Derby black-black  Calfskin View 40
Mens Crossover™ Derby black-black  Calfskin View 41
Mens Crossover™ Derby black-black  Calfskin View 42
Mens Crossover™ Derby black-black  Calfskin View 43
Color Black | Black
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COMPLETE THE LOOK
From shoe fit to outfit perfection, we've got you covered! Our Wolf & Shepherd Footbeds ensure all-day comfort. Pair it seamlessly with our premium leather Stealth Belt.
Details
  • Full-grain Italian calfskin upper
  • Removable memory foam footbed for industry-leading comfort
  • Memory foam padded scuba lining
  • Leather treated with custom-blended formula to improve softness and durability
  • Ultra cushy EVA midsole
  • High-traction, thermal rubber outsole
  • Wax-coated flat athletic laces
Highlights
  • All-Day Comfort For Your Feet
  • Premium Italian Leather
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  • Removable Footbed
Fit

Runs true to sneaker size. Take your true sneaker size for a comfortable, glove-like fit. These will give with time and mold to the shape of your foot. 

Note: We recommend ordering up half a size from your Wolf & Shepherd dress shoes.

In between sizes? Our Premium Footbeds come in Narrow and Wide, allowing you to customize your fit.

Best Worn With

The Crossover™ Derby

Business, Meet Casual

Whether you’re navigating a busy workday or stepping out for an event, the Crossover™ Derby provides the perfect balance of sophistication and comfort for any occasion. Handcrafted from full-grain Italian leather, the Derby features a high-performance sole that adds an extra step of athleticism to your dress shoes. This innovative design incorporates a sleek silhouette with a unique crossover detailing, offering a modern twist on the classic derby-style shoe. With its lightweight construction and responsive sole, this crossover dress shoe is designed to keep you feeling agile and confident, making it an essential addition to your wardrobe!

The Future of Footwear

Game for Anything

Equal parts poise and performance, these hybrid dress shoes are built to bridge the gap between work and play. Featuring a lightweight construction, shock-absorbent cushioning, and premium Italian leather, the Crossover™ gets you where you need to go – no matter the route you take. With this shoe, you’re always game for anything life throws your way.

Italian Leather Upper

A Luxury Finish With No Break-In Time

Celebrate the unique properties and depth found in full-grain Italian leather. Slight color and finish variations are natural and occur when our artisans hand-finish each product, giving each shoe a perfect look and feel with no break-in time needed! Enjoy the rich color, natural creamy finish, and wax coated shine found in each pair of our derby shoes.

Cushioned Removable Insoles

Like Walking on Clouds

Our removable footbeds feature dual-density memory foam layers lined with supple sheepskin leather for maximum comfort. If you need to adjust sizing a bit, just snag one of our Wide or Narrow footbeds. Wolf and Shepherd’s proprietary footbed can also be taken out and replaced when they wear down.

A Refined Silhouette

The Next Level of Professional Footwear

Crossover shoes are redefining workplace footwear by offering a more casual alternative to standard dress shoes. Their adaptability allows you to express your personal style while maintaining a polished look. We think they pair best with chinos, khakis, and denim styled with a nice sport coat.

Explore our style guide to discover the many ways you can incorporate our men's crossover dress shoes into your wardrobe and embrace a new era of footwear that prioritizes both style and comfort.

Wolf and Shepherd Crossover™ Derby

The Perfect Blend of Comfort and Sophistication

Experience the art of fine craftsmanship with the Crossover™ Derby – where elegance meets functionality. Crafted from high-quality materials and featuring a unique crossover design, this hybrid dress shoe elevates your look while providing exceptional support and breathability. Whether you're heading to the office or enjoying a night out, the Derby adapts effortlessly to any occasion!

Step confidently into any moment with Wolf and Shepherd! Shop our entire collection of Crossover™ shoes today.

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Choose your gift

Free with purchase of any full-price shoe
Pickleball Set
Track Jacket
W&S Slim Wallet
Shoe Care Kit
Pickleball Set
Track Jacket
W&S Slim Wallet
Shoe Care Kit
Sneaker Shoe Care Kit
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Pickleball Set
Hit the court in style with the limited edition Wolf & Shepherd Pickleball Set. With two signature rackets and a stylish go-bag, this set will have you looking as good as you play.
Navy Navy Navy
Track Jacket
Experience the luxe comfort and subtle style of our limited-edition Wolf & Shepherd Track Jacket.
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W&S Slim Wallet
Designed to carry your essential cards and folded bills, so you can reduce bulk in your pocket to preserve clean garment lines.
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Shoe Care Kit
Everything you need to keep your Crossover™ shoes in winning shape. This all-in-one kit comes fully equipped to clean and protect your leather uppers and keep your soles bright.
Storm Storm Storm
Sneaker Shoe Care Kit
Everything you need to keep your sneakers and accessories looking their best.

Size guide