A landmark of late-night television went down on Monday night, when David Letterman joined Stephen Colbert on The Late Show, the enormously popular evening talk show that the former hosted for more than two decades. It was the first time Letterman had returned to the series as a guest after departing—a conspicuous absence that many commentators credit to some ill-feeling over how Colbert was handed the reigns in transition. Though Letterman and Colbert did not end up discussing the controversy over the course of their 20 minute interview, they had a warm and lively chat that suggested they’ve since cleared the air.
But as nice as it was to see one of the greatest late night talk show hosts of all time back on home turf, it was his arrival outside the Ed Sullivan Theater, the long-time Late Show studio, that made the most immediate impression. Sporting a purple and yellow beanie, a weather-beaten Carhartt jacket, bootcut jeans, a well-loved wax canvas duffle, and a pair of olive green Zeha Berlin football shoes, the legend wasted no time to remind us that David Letterman has always been a style icon—whether riffing in the studio, waltzing through an airport terminal, or fly-fishing in Upstate NY. This is how you dress for November in New York: crisp but rugged, warm but with some bright pops of color. (It helps if you’ve got a mile-long white beard, but it’s not mandatory.)
It’s worth noting that these Zeha Berlins have been popping up a lot lately: singer-songwriter and producer Jack Antonoff even wore a pair of his own on the Tonight Show earlier this month, making them a sudden and unexpected late night staple. The somewhat obscure German vintage footwear brand, founded in the late 19th century, has been making a steady comeback over the last several years as they’ve been re-releasing vintage football silhouettes with a whole lot of nostalgic appeal. Letterman’s got the right idea: they pair with dark denim and a light jacket perfectly, and are ideal for an autumn day with good weather.