“Little kids are fucking anarchists, they don’t give a shit,” says Jeremy Smith, the co-founder of Berkeley menswear mecca Standard & Strange. “I always try to remember that. When you’re a little kid, you’re wearing your yellow rain boots and a skirt and, like, half a Halloween costume. It’s beautiful.”
Don’t confuse affectation with style
Style about being unafraid to like what you like, even if it isn’t trendy or popular. It’s also about an entire wardrobe, not just one element. “When I was in college, there was a guy who was very prosaic-looking, but he wore a cowboy hat,” Boyer recalls. “It wasn’t style, it was eccentricity, and there’s a difference. Style is something that permeates your life. Otherwise, it’s just kind of weird.”
Walk the line between inspiration and imitation
“A lot of people want to dress like Steve McQueen, but most of these icons were just wearing the clothes that they had around them, they happened to be in good shape, and they bought clothes that fit. That’s it. No secret sauce,” says Smith. “I appreciate having those waypoints in style, and you can always use that as a reference for ideas, but to just imitate it puts you in a very cosplay position because it’s not authentic. It’s not coming from within.”
Style can mean wearing the same thing every day
Personal style is all about figuring out what works for your taste and your life. For some of the world’s most stylish dudes, that means narrowing down your wardrobe down to a signature look—see Bill Cunningham’s iconic chinos and bleu de travail or Cornel West’s three-piece black suit—and wearing it on repeat. “I love the concept of a uniform,” Belgue says. “Tailoring, authenticity, and quality are the keys to getting it right. Beyond that, the world is your oyster.”
Beware of self-proclaimed style gurus
“Oftentimes these guys on Instagram or YouTube who are trying to teach style are really talking about how they like to dress and presenting it as these universal laws,” Smith says. “Don’t let anyone try to tell you what to do.” Instead, he suggests poring over books like Alan Flusser’s Dressing the Man and photos of artists and musicians from the pre-internet age. “You can look at these as an archive of very authentic ways of dressing that aren’t about dressing for a camera.”
When in doubt, defer to Ralph
“Ralph Lauren has a great integrity about his sense of style, because when the whole world was turning towards the Italians and those short little tight suits and so forth, he remained a kind of Anglo-American Ivy guy,” Boyer says. “In half of the pictures you see of Ralph, he’s either wearing his old black and white tweed herringbone sport jacket, or a double breasted blazer. I think there’s a certain authenticity and integrity about that.”
Start with the classics
Ready and raring to begin building a proper wardrobe that feels entirely your own? Here are a few time-tested menswear staples to serve as a strong foundation—and don’t miss our comprehensive guides on closet essentials, office wear, winter style, and 2025’s biggest trends for even more can’t-miss shopping intel.
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