- Premium Full-grain 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
- Imported
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
$275
Sale price
$275
Regular price
Unit price
per
Details
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.
Stealth Leather Dress Belt
Regular price
Starting at $63
Regular price
$125
Sale price
Starting at $63
50% OFF
Unit price
per
W&S Footbed
Regular price
$40
Regular price
Unit price
per
Highlights
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All-Day Comfort For Your Feet
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Premium Italian Leather
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Free Shipping
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Removable Footbed
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Hand Crafted
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
- Chinos
- Commuter Pants
- Joggers
- W&S Footbed
Fit & sizing
Get the size right the first time
80%
Say true to size
227
Verified fit reviews
30
Days free exchange
Step 1 — Fit report
10%80% true to size10%
Runs small — size upRuns large — size down
- Runs small
- True to size
- Runs large
Step 2 — Why it fits the way it does
Crossover Derby
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Width
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Instep volume
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Heel hold
- Size range US Men's 7–15, half sizes from 7–12
- Insole at US 10 288.5 mm
- Break-in Breaks in within 1–14 days.*
What we'd tell you to order
- Standard foot Your usual size
- Wide foot Size up a half size
- Thicker socks Your usual size
Coming From Another Brand
Wolf & Shepherd Men's US size 10 offers a comparable fit to the following footwear brands:
- Nike US 10
- On US 10
- Allen Edmonds US 10
- Cole Haan US 10
Step 3 — The details, if you want them
How our styles differ
How this compares to our other styles
The sock weight this fit is dialled for
Exchanges
Step 4 — Still deciding? Pick one
30 seconds
Find my size
Three taps — your usual size, the brand you wear now, how you like a shoe to fit. We return one size and show the reasoning.
Chat with an expert
Our Care Team is available Monday–Friday, 8:30 AM–5:00 PM PT, to assist with sizing and fit questions and help you find the right fit.
Our AI-powered specialists are available 24/7 to help with sizing and fit questions, so you can find the right fit with confidence.
Either way, if the size misses we exchange it free — both directions, for 365 days.
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.
Fit finder