NYC designer Mark McNairy pairs up with New York label Engineered Garments for this eyebrow raising Long Wing Boot. While it may look fairly traditional from afar, the American derby style boot actually has an interesting twist, where they switch up the leather on the wing and the upper from boot to boot. Meaning one boot has a grain leather wing and plain calf upper, and the other shoe is inverted: grain upper and plain calf wing. The wingtip-looking boot is bench made in northern England and comes with a Goodyear welted double leather sole. Available now at Tres Bien for $500 (€ 392).

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