David Letterman, arguably the greatest bearded entertainer in television history, might not be known for having an eclectic and desirable sense of style, but as the 76-year-old arrived at The Late Show with Stephen Colbert on November 20, you’d be forgiven for thinking is.
The famed TV presenter, who hosted no less than 6,080 episodes of Late Night and Late Show, rolled up to his old stomping ground in New York City donning a classic Carhartt WIP chore jacket, striped beanie, and denim pants as a part of an ensemble that is perhaps Letterman's most stylish in decades (ignoring his one-off YEEZY makeover, of course.)
The look, while not reinventing the workwear wheel, put a solid smile on my face when it appeared on my social feeds on the morning of November 21, and saw Letterman jump straight to the top of my old man style muse list.
Joining the likes of Harrison Ford and Bryan Cranston on my exclusive directory of well-dressed older men, Letterman finished off his look by perfecting the finer details: tinted sunglasses, a leather-bound holdall, and some magnetic spectacles hooked around his neck.
Sure, there's room for improvement, particularly in Letterman's choice of footwear. The sneakers, while not ruining the outfit by any means, look almost wood-like. Perhaps akin to a pair of creps you’d find Pinocchio knocking about in, or a young war evacuee in the early 1900s.
Still, for Letterman bad shoes can be excused, especially when the rest of the ‘fit is so on point.
Truth of the matter is, if I look half as good as Letterman does in casual workwear when I’m creeping towards the tender age of 80, I’ll be a very happy and very stylish old guy. That's the goal anyway.
