The Twofer: Old-School Tennis Cool Edition

A convertible to get to the courts, and sneakers that won’t scuff.

Mr. Porter

Tennis: a sport America loves, at least when Serena Williams is playing. It’s fantastic fun! Don’t say “zero,” say “love.” Don’t use a “racket,” use a “racquet.” Don’t drink beer, sip gin! Most courts ban marking soles, and some require all-white outfits—collars, too. So, a lot of rules, harking back to game’s origins as a lawn game for British aristocrats, but all worth it for the satisfying thwomp of a well-hit ball and the chance to “accidentally” nail your doubles partner with a backhand in the groin. And, as with Western Civilization’s stuffier traditions, there’s joy in being a little subversive.

Take these tennis shoes. They’re made by Nike—who we hear is an established equipment supplier, in addition to being a Serena Williams sponsor—and sport non-marking rubber soles and a demure silhouette. Even the stuffiest club would be hard-pressed to protest these kicks, even as they shirk tradition. Instead of white canvas, these Nikes come in beautiful navy leather, with the classic swoosh rendered in perforations along the side. They’re up to code, but cool enough to ruffle feathers.

ebay

Same with this 1958 300SL. It’s white paint is entirely appropriate, and nothing garners respect at a country club like a vintage Mercedes. But this unpolished jem has the touch of scruff on the neck, and its Oxford has holes. Unrestored through over 50 years of use, the Benz wears a perfect patina. The blood-red leather is cracked, and the ivory paint has seen some sun. We’d suggest underscoring its ratty vibe with a burnout as you head home after the match.