How to Find Your Personal Style, According to Menswear Experts
StyleNo one can teach you exactly how to look effortlessly put together, but figuring it out for yourself just requires a bit of trial and error.By Jeremy FreedJanuary 27, 2025Photographs: Getty Images; Collage: Gabe ConteSave this storySaveSave this storySaveAll products are independently selected by our editors. If you buy something, we may earn an affiliate commission.The most stylish guys in the world don’t all dress the same, but they do share one important thing in common. Whether it’s Chris Pine’s West Coast boho, Tyler, the Creator’s freaky streetwear edit, or Bill Nighy’s wardrobe of perfectly tailored suits, the thing that bestows each of these style icons their gravitas is a unique sartorial point of view that reflects their taste and personality.The hitch? Personal style isn’t something that can be bought or taught. “Style isn't for sale in the shop window,” explains veteran menswear writer Bruce Boyer. With some keen observation and a little trial and error, however, anyone can create a signature style for themselves. “Style is something that you create through the will of your personality,” Boyer continues. “You take what's out there in your world and you try to mold it and bend it and turn it to fit you.”With that in mind, we polled a few of the most stylish guys we know to weigh in on the topic, and distilled their collective wisdom into a few essential points.Style isn’t fashionStyle is about liking what you like, and fashion is about liking what other people want you to like. That’s because fashion is created by designers and brands who need to sell a certain amount of new clothes every season to keep their businesses going. There’s nothing wrong with this in principle (clothing is a basic human need, after all) but style is less about what a designer or brand is pushing this season, and more about what resonates with you on a personal level.“Personal style is an expression of your true self, and tends to reflect how you feel most comfortable and most natural, and fashion is reacting to a marketplace impulse. One is internal, one is external,” says Mike Belgue, the brand director at Reigning Champ. “Besides not needing to pivot every time the marketplace sneezes, personal style is a reflection of your most confident state.”Style is identityYour life, your background, the places you’ve been, and the experiences you’ve had are the building blocks of personal style. Ask anyone whose style you appreciate and they’ll likely have a story about an experience that influenced their taste and shaped their wardrobe.“I went to an all-boys Catholic school and we wore a uniform every day: a navy blazer, a white shirt, a navy tie, and gray trousers,” says Steve Knorsch, the managing director of Cad & The Dandy in NYC. “I still wear some version of a navy blazer and gray slacks at least once a week. It’s such a perfect combination that never looks outdated.”Inspiration can come from unexpected placesCelebrities are an easy source of inspo, but their red carpet fits are just as likely a result of their stylist’s taste as their own. Regular people, on the other hand, can offer more authenticity (and often bolder choices.)“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 styleStyle 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 dayPersonal 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
All products are independently selected by our editors. If you buy something, we may earn an affiliate commission.
The most stylish guys in the world don’t all dress the same, but they do share one important thing in common. Whether it’s Chris Pine’s West Coast boho, Tyler, the Creator’s freaky streetwear edit, or Bill Nighy’s wardrobe of perfectly tailored suits, the thing that bestows each of these style icons their gravitas is a unique sartorial point of view that reflects their taste and personality.
The hitch? Personal style isn’t something that can be bought or taught. “Style isn't for sale in the shop window,” explains veteran menswear writer Bruce Boyer. With some keen observation and a little trial and error, however, anyone can create a signature style for themselves. “Style is something that you create through the will of your personality,” Boyer continues. “You take what's out there in your world and you try to mold it and bend it and turn it to fit you.”
With that in mind, we polled a few of the most stylish guys we know to weigh in on the topic, and distilled their collective wisdom into a few essential points.
Style isn’t fashion
Style is about liking what you like, and fashion is about liking what other people want you to like. That’s because fashion is created by designers and brands who need to sell a certain amount of new clothes every season to keep their businesses going. There’s nothing wrong with this in principle (clothing is a basic human need, after all) but style is less about what a designer or brand is pushing this season, and more about what resonates with you on a personal level.
“Personal style is an expression of your true self, and tends to reflect how you feel most comfortable and most natural, and fashion is reacting to a marketplace impulse. One is internal, one is external,” says Mike Belgue, the brand director at Reigning Champ. “Besides not needing to pivot every time the marketplace sneezes, personal style is a reflection of your most confident state.”
Style is identity
Your life, your background, the places you’ve been, and the experiences you’ve had are the building blocks of personal style. Ask anyone whose style you appreciate and they’ll likely have a story about an experience that influenced their taste and shaped their wardrobe.
“I went to an all-boys Catholic school and we wore a uniform every day: a navy blazer, a white shirt, a navy tie, and gray trousers,” says Steve Knorsch, the managing director of Cad & The Dandy in NYC. “I still wear some version of a navy blazer and gray slacks at least once a week. It’s such a perfect combination that never looks outdated.”
Inspiration can come from unexpected places
Celebrities are an easy source of inspo, but their red carpet fits are just as likely a result of their stylist’s taste as their own. Regular people, on the other hand, can offer more authenticity (and often bolder choices.)
“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.
