McHale admits he has always cared about his appearance – "probably stupidly so," he says – and yet he gives no credence to men who claim to rise above fashion. "If guys really didn't care, they would wear, like, a torn sport coat with an Iowa sweatshirt and a skirt," he says. "Even if you wear the same thing every day, you're still actively trying to communicate a certain look." In his case, McHale is especially fond of New York-based Isaora, a company that he says makes pieces "inspired by snowboard clothing, all very cool and fashionable." When it comes to suits, he's a fan of Calvin Klein, for style and material, but also fit – always a tall order for a very tall guy.
Mad Men's Charming Rogue
The man who played Roger Sterling, is moving on – surfing in Montauk, hanging with his son, and directing a feature film.
Plus: Greenpeace's High-Seas Avenger
ON NEWSSTANDS NOW
What's on John Slattery's Mind
Willem Dafoe's Life Advice
Sign up to receive the Men’s Journal newsletter and special offers from MJ and its marketing partners.