First, a confession: There’s no such thing as dressing “timelessly”. If you’ve paid any attention to, say, the way politicians dress vs. the way Tom Brady dresses, or the way Benedict Cumberbatch dresses (or maybe how Cary Grant once did), you’ll know that there’s no single way to dress, because fashion is constantly influencing the clothes that men wear.
Take the above example of politicians vs. people who look better than them, and you’ll quickly see why you can’t just dress the same way forever: eventually you look like an out-of-touch fossil—and perhaps out of touch, not just with fashion, but with society in general. If that’s a bad look for a politico, think how terrible it’ll make anyone else look, too.
Still: There’s an art to building a wardrobe with elements you won’t have to replace every season. To learn that art, we asked Bonobos’ Chief Creative Officer Dwight Fenton, a 20-year style veteran who’s also worked at Patagonia and J. Crew.
Fenton’s main concept: The modern way to consistently dress well is to mix casual pieces with more formal ones. In fact, being just slightly “off-trend” is what timeless dressing is all about. Your sense of style should be about self-expression, not total conformity. Observe the trend without being a slave to the moment. That’s something any guy can do with straightforward, foundational clothing.
Here are 10 tips you can use to dress well—and maybe even a little bit “timelessly”.