Not a sneaker, not a dress shoe. That gap is where most men over forty actually live, and almost nobody makes a shoe for it. Split leather upper, a stitched apron seam across the toe, and a gum rubber sole you can walk a city in.

• Apron toe with a raised saddle seam
• Gum rubber sole — grip, no clatter
• Leather lined, three-eyelet open lacing
• Split leather, so it won't patina like full grain

Fit: true to size. Roomy through the toe