Mephisto shoes are treasured for their comfort and stubbornly unfashionable authenticity. Photo: Alexandra Nataf/Wenzel & Co Mephisto, the ultimate grandpa brand, is suddenly, improbably cool.

If Mephisto was game to work with Mr. Procell, it was in part because the company has arrived at a moment when the shoes’ stodgy nature is making them desirable.

ORTHOPEDIC-CHIC Four comfy and appealingly untrendy pairs of shoes that might entice both great-uncles and millennials. From left: Mephisto Shoes, $235, endclothing.com; Shoes, $225, keenfootwear ...

Mephisto’s history goes back to 1965, when Martin Michaeli, who had spent time in New England with shoe makers, wanted to create a footwear brand.