Over the course of this column, I’ve advocated for men to take a few chances we want to expand our horizons, after all. In short, we’ve all aimed too close to the sartorial sun. The rest of us can pray the offending image is buried deep in the minds of friends and family (and the Google archives). If you’re lucky, you didn’t make this error while attending the Academy Awards. The intention might have been good, but context, fit and trend conspired to leave you humbled. There might be a pinstripe suit that seems a little too graphic once you’ve stepped away from Savile Row that’s now relegated to a John Dillinger–esque Halloween costume. When you return home, your beret suddenly makes less sense when you’re no longer enjoying a glass of Sancerre at the Café de Flore (I’m not sure how hot it looked even while you were in Paris). This is why you should never buy a hat while on holiday. How do they happen? Well, often a mistake starts from a place of experimentation, of confidence and, dangerously, of sartorial zeal. These clothes seem to have been acquired by some other human with demonstrably worse taste than oneself (isn’t that always the way?). There might be something he vaguely remembers buying that shimmers or flares, something recommended by a persuasive sales associate. Staring back at him is a bombastic tie, an overly daring shirt or, lord have mercy, a pair of leather pants. There comes a time in every man’s life when he looks into his closet and doesn’t like what he sees.
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