Wolf & Shepherd

The quest to take the pain out of wearing men’s dress shoes isn’t new, but Wolf & Shepherd takes things to the next level with memory foam, carbon fiber, sheepskin, and oh my god look at those blue leather monk straps.


Photo: Wolf & Shepherd

With no breaking in and wearing the thinnest pair of dress socks I own, I spent the day in Wolf & Shepherd’s Gambit Double-monks, and suffered no consequences for my bravado. The toe box was tight at first, a perennial problem for me, but the soft leather broke in almost immediately.

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Wolf & Shepherd’s shoes are stacked with tech, but the soft sheepskin lining, weight reduction that the carbon fiber delivers, and of course the memory foam footbed are what you’re really going to notice.

At this level of style, these price points, and with these aims, comparisons to Cole Haan are unavoidable, and that’s some damn good company to be in. The feel and quality are close enough that I’d have to tell you to just buy the shoe you like the look of better, or both!


Photo: Wolf & Shepherd

I also checked out Wolf & Shepherd’s Gunner Drivers, a pair or driving loafers with the same tech as the rest of their shoes. Loafers are already pretty comfortable in general, but these are particularly so, complete with water resistant leather.