Shortly after arriving in New York I developed a men’s style column at The Huffington Post which lasted for a short time. This article on the rules of dress is still up on the site and I think is worth revisiting at a moment in time when standards of dress are in grave danger. (You can check out my storybook “These Are Our Failures,” released precisely one year ago, for my full thoughts on the state of masculine elegance.)
In my experience, rules-obsessed dressers are lacking in natural style and charisma, surely know this, and must get an ego boost from the thought that they dress “correctly.” In contrast, those who are naturally stylish tend to go for the general feel of clothes and don’t sweat the details much. I think of Chet Baker donning his girlfriend’s sweater, as recounted by Charlie Davidson in my recent Rake article, who said, “The goddamn thing looked great on him.” Surely wearing women’s clothing breaks most men’s commandments about correct gentlemanly attire.
Here’s a snippet:
“Pulling something off” — say, a chesterfield coat over an oxford shirt and gray sweatshirt, paired with jeans and bit loafers and accessorized with a baseball cap and toasted bagel — is something that really gets the prescriptivists’ boxers in a bunch, for pulling something off requires breaking rules.
Head over here for the full story, which includes some quotes from Alan Flusser, who for much of his career was seen as the arch arbiter of rules, but who has mellowed considerably with age. — CC