Crossover™ Loafer

A classic penny loafer reimagined with sleek style and comfort in mind.

Regular price $279
Sale price $279 Regular price
Final Sale ?

This item is NOT valid for Exchange or Refund. Final Sale Items may NOT be exchanged or returned for store credit. No refunds or exchanges will be issued.

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Color Black | White
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  • Full-grain Italian leather upper
  • Removable memory foam footbed for industry-leading comfort
  • Foam-injected scuba lining for comfort and moisture wicking
  • Leather treated with custom-blended formula to improve softness and durability
  • High-density TPU sole
  • High-traction, thermal rubber outsole
  • Designed in collaboration with Steve Nash
  • Made in Portugal
  • cushion logo
    All-Day Comfort For Your Feet
  • handcrafted logo
    Premium Italian Leather
  • MadeInPortugal logo
    Made In Portugal
  • FreeShipping logo
    Free Shipping

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 a half-size up from your Wolf & Shepherd dress shoes.

Best Worn With
  • Chinos
  • Trousers
  • Jeans

See how we style the Crossover™ Loafer in The Playbook.

Business, meet Casual.

Meet the ultra-cozy Crossover™ Loafer: A slip-on dress shoe for the modern working man. Retooling what it means to be business casual, these loafers feature Wolf & Shepherd’s proprietary memory foam footbed and full-grain, Italian leather finish. Feel boardroom-ready with a dress shoe that wears like your favorite sneakers.

A luxury finish with no break-in time.

italian leather upper

Our Crossover™ Loafers are made with the finest leather imported from Italy and are hand-cut by craftsman in Portugal. Each hide is 60% vegetable-tanned, 40% chrome-tanned giving our shoes a perfect look and feel. No break-in time needed.

Like Walking On Clouds

Cushioned removable insoles

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

The next level of professional footwear.

a refined silhouette

We designed the Crossover™ Loafer to fit both home and work environments. The low vamp and wider mid-foot makes it easy for you to slip these on and off while giving your toes room to breathe.


Size guide