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Much as we love the sneaker/oxford crossover, it’s important to do it in the right way. Otherwise you end up with…well, this.

Heyday Footwear has been pushing a “wingtip-inspired sneaker” called the Winger, and it’s a sign of what happens when the crossover goes awry. Instead of taking the classic wingtip form and giving it a some of the pop glossiness of a sneaker, Heyday just makes the shoe softer, squishier, and less useful.

The result is the worst of both worlds. Too casual for suits and too stilted for jeans, this is a good idea gone bad.

—R.B.

CONTRIBUTORS

  • Russell Brandom