The Most Stylish Men of All Time

the most stylish men of all time

From Hollywood A-listers to sports stars, we pick the most stylish men of all time and check out the distinct looks that have made them the male fashion icons of our time. 

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Style is subjective, but what we can all agree on is that some men in the world have a knack for getting it right more often than the rest of us simple souls. You, no doubt, have people you look to, whether it’s on social media or television, for some style advice or inspiration, but this guide is going to narrow down some of the most stylish men in the world and how you can get their style.

Cameron Dallas

Social media star and new kid on the scene , Cameron Dallas has the hearts of every teenage girl across the world swooning. Known for his laid back and relaxed style, Cameron Dallas emulates the casual cool of L.A.. More commonly seen in a pair of simple jeans and a T-shirt, but not afraid of a slick suit, Cameron Dallas’ style is easier to emulate than you might first think.

cameron dallas navy suit mens street style
PHOTO CREDIT: Pinterest

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How to Get Cameron Dallas’ Style

To achieve the casual style that Cameron Dallas is known for then simply pair a plain white T-shirt and some black jeans with a casual trainer. You can accessorise a little bit with a jacket or some jewellery, but if you want to keep it simple then stick to the basics.

cameron dallas street style for men
PHOTO CREDIT: Teen Vogue

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Conor McGregor

UFC fighter Conor McGregor is known for his skills in the ring, but he’s also know for his extravagant and outlandish style outside of it as well. Sharp suits and bold colour are the backbone of Conor McGregor’s wardrobe whilst investing in classic pieces to see him through every season with ease.

conor mcgregor suit mens street style
PHOTO CREDIT: Las Vegas Weekly

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How to Get Conor McGregor’s Style

However, it’s not all bold pattern and vibrant colour that dominate McGregor’s wardrobe, he is a fan of a more subdued and simple looks. A classic pair of raw denim jeans and a simple jumper in a slim fit will help you emulate this Dublin native’s wardrobe.

conor mcgregor style
PHOTO CREDIT: Pinterest

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Jaden Smith

Son of the much loved actor and comedian, Will Smith, Jaden has certainly made a name for himself in Hollywood. You probably remember first seeing him in the emotional The Pursuit of Happiness or The Karate Kid, but it’s not his acting skills that we’re focusing on, it’s his style.

jaden smith bomber jacket
PHOTO CREDIT: Pinterest

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How to Get Jaden Smith’s Style

Laid back and typically L.A., Jaden’s style has been known to take many forms. Most recently his campaign for Louis Vuitton Womenswear made headlines for its gender-bending ideologies, but Jaden Smith’s everyday style is usually consistent of black jeans and a slouchy T-shirt teamed with a pair of trainers.

jaden smith t-shirt
PHOTO CREDIT: W Magazine

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David Beckham

Probably the most relatable and revered men on this list, David Beckham epitomises a classic and no-nonsense way of dressing. Known for fitted styles with classic pieces mixed in with a few heritage items, David Beckham’s style is easily achievable and extremely stylish.

david beckham ray ban wayfarer sunglasses black polo shirt for men
PHOTO CREDIT: Pinterest

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How to Get David Beckham’s Style

With David Beckham’s style, you have to remember to always rely on your basics and then incorporate trend lead pieces in with them. A great look that David Beckham look is teaming a simple jumper with a pair of chinos and trainers.

david beckham striped t-shirt mens street style
PHOTO CREDIT: Wear It Like Beckham

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Tom Hiddleston

Better known as Loki in the famed Marvel films, Tom Hiddleston channels a very classic approach to his wardrobe while maintaining a stylish yet modern look. If he’s not in costume or casual clothing Hiddleston can be seen in a suit looking tailored and sharp. With a penchant for navy, Hiddleston channels a classic English gent but challenges the norm with a pair of black patent shoes.

tom hiddleston navy suit mens street style
PHOTO CREDIT: Pinterest

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How to Get Tom Hiddleston’s Style

For a more laid back look whilst still channelling Tom Hiddleston’s style, take a simple black or dark jumper and team it with a pair of casual trousers of the same hue. Throw on a pair of boots and accessorise with a pair of sunglasses and you’ll be channelling Tom Hiddleston in no time.

tom hiddleston black jumper and trousers mens street style
PHOTO CREDIT: Pinterest

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Johnny Depp

Better known for his talents for acting, Johnny Depp has also made headlines for his quirky take on style. A fan of the more bohemian pieces out there, with flared jeans, neckerchiefs and wide brimmed hats, Johnny Depp has an affinity for challenging the social norms of menswear, and we love it.

johnny deep t shirt and jeans mens street style
PHOTO CREDIT: Get The Label

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How to Get Johnny Depp’s Style

Of course, not everyone shares the same taste as Johnny Depp so trying to emulate his style can be quite tricky if you’re a fan. However, Johnny isn’t shy of something simple, so you can try wearing a simple white T-shirt with a pair of classic blue jeans. Johnny Depp is an avid fan of accessorising, but again, it’s an acquired taste, so start out by wearing a simple yet classic watch to top the outfit off.

johnny depp white t shirt and jeans mens street style
PHOTO CREDIT: Pinterest

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Ryan Gosling

One of Hollywood’s leading actors, Ryan Gosling, is better known for making hearts swoon globally with his envious good looks and romantic acting, but it’s his casual approach to dressing that we’re interested in. Not one to go wild with pattern or colour, Ryan Gosling’s style is more subdued and unassuming; pairing classic pieces together

ryan gosling cannes film festival white shirt trousers mens street style
PHOTO CREDIT: Style Forum

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How to Get Ryan Gosling’s Style

Ryan Gosling is definitely a fan of the 70’s as it’s clear is his colour choices and styling. The 70’s was all about subdued colour and wide collars and flares; now I’m not condoning you sport a pair of flared trousers, but wide collar shirts, or cuban collar shirts, are having a big resurgence, so now’s the best time to jump on the trend train.

ryan gosling black suit yellow shirt mens street style
PHOTO CREDIT: Looktastic

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A$AP Rocky

A$AP Rocky is one of the biggest names in hip-hop at the moment. His music speaks to millions of fans globally, and his sense of dressing has earned him the front row of major fashion shoes across the world. As the face of Dior Homme, A$AP Rocky has cemented his place in the style stakes.

asap rocky black brogues mens street style
PHOTO CREDIT: On Point Fresh

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How to Get A$AP Rocky’s Style

Usually known for going a little wild when it comes to his personal style, it’s always a breath of fresh air when A$AP turns up in something quite unassuming. Seen here with a classic white button down and black jeans, he channels a more alternative look whilst still keeping it smart and put together.

asap rocky black jeans saint laurent boots black coat mens street style
PHOTO CREDIT: Pinterest

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Luke Evans

Welsh actor Luke Evans is better known for playing Greek gods, Vampires, and most recently, Disney villains, but his unassuming, laid back style resonates with most men out there. Pairing classic basics with more statement jackets and coats, Luke Evans creates a fun and unique sense of dressing with minima effort.

luke evans green jacket white t shirt mens street style
PHOTO CREDIT: Electric Sekki

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How to Get Luke Evans’ Style

Opting for tailored pieces over slouchy styles, Luke Evans’ style is classic whilst mixing in some trend lead, more statement pieces. For a great winter look, take a simple black roll neck jumper and throw over a statement coat; team with jeans and a pair of boots for a simple, understated and stylish look.

luke evans black roll neck jumper grey coat mens street style
PHOTO CREDIT: Pinterest

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Tom Hardy

Mad Max actor and dog lover Tom Hardy is better known for playing some of the toughest roles in Hollywood, but his soft spot for his style, and man’s best friend, is what we’re talking about. Usually seen on the red carpet in a sharp suit, Tom Hardy is a man who knows how to dress for himself.

tom hardy navy suit blue shirt mens street style
PHOTO CREDIT: Daily Siren

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How to Get Tom Hardy’s Style

Taking inspiration from his double role as the infamous London gangsters, the Kray Twins, Tom Hardy always gives a subtle nod to the 50’s and 60’s when he puts on a suit. To emulate, take a classic white shirt and team it with a simple black suit; throw on a formal shoe, such as a loafer or brogue and you’ll be set to go.

tom hardy white shirt black tie mens street style
PHOTO CREDIT: Get The Label

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Harry Styles

With influences from Mick Jagger and Keith Richards cropping up in Harry Styles’ style, he has fast become of of the most stylish men on the planet. With bands such as Saints Laurent, Gucci and Haider Ackerman featuring heavily in his wardrobe, Harry Styles has carved out a pretty impressive rosta of looks he can fall back on.

harry styles white shirt black jeans boots mens street style
PHOTO CREDIT: Pinterest

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How to Get Harry Styles’ Style

More commonly seen in a casual ensemble, Harry Styles is a massive fan of black skinny jeans (ripped or not), a loose, casual shirt all topped off with a pair of boots. This uniform has seen Harry Styles go from small schoolboy, thrusted into the spotlight through reality television to global superstar who can rely on some of the biggest fashion houses to dress him for red carpets. Harry Styles is certainly a contender for the most stylish man in the world.

harry styles black jeans bornw boots mens street style
PHOTO CREDIT: Pinterest

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Leonardo DiCaprio

One of the most famous actors in the world, Leonardo DiCaprio has carved out an extremely impressive career. His roles in Titanic and The Wolf of Wall Street certainly show off his acting credentials, but his style, both on and off the red carpet give reference to his sense of dressing as well.

how to dress like Leonardo Dicaprio
PHOTO CREDIT: Pinterest

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How to Get Leonardo DiCaprio’s Style

Definitely one to shy away from the paparazzi, Leonardo almost always takes an extremely laid back and achievable approach to style.  Seen here in a simple shirt and jumper with a pair of jeans, Leonardo DiCaprio’s style is definitely comfortable and easy to wear.

leonardo dicaprio mens street style
PHOTO CREDIT: Pinterest

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Eddie Redmayne

Talented actor and former model Eddie Redmayne has made a name for himself playing challenging roles on screen, but his time as a former model for British fashion powerhouse, Burberry and his enviable and classic style of dressing is what got us talking. With a quintessentially English approach to dressing, Eddie Redmayne ranks quite highly in the style stakes for his no nonsense approach to menswear.

Eddie Redmayne Burberry SS12
PHOTO CREDIT: Burberry

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How to Get Eddie Redmayne’s Style

Always smart, Eddie Redmayne relies on his classic basics to see him through most formal and casual occasions. Seen here with a simple shirt and jumper combination teamed with a pair of grey trousers and a formal shoe, Eddie is a beacon of classic dressing for men.

eddie redmayne style
PHOTO CREDIT: Pinterest

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Justin Bieber

Controversial character and style chameleon, Justin Bieber, has certainly made the headlines in recent years for the wrong reason, but his style is undeniable and Bieber knows how to nail the biggest trends of the time with ease. A fan of anything oversized, Justin Bieber’s style has certainly evolved, but he stays true to what he loves.

justin bieber navy suit mens street style
PHOTO CREDIT: Teen Vogue

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How to Get Justin Bieber’s Style

Every time Justin steps out onto the red carpet you don’t know what you’re going to be seeing. he might channel something classic and understated for one event, then mix it up by letting his hair down and going for a more alternative look with a leather jacket and jeans.

jusitn bieber saint laurent leather jacket blue jeans mens street style
PHOTO CREDIT: Teen Vogue

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Drake

Hotline Bling singer and Canadian native, Drake, certainly knows how to fill the dance floor at pretty much every club around the world. After his body transformation to a more leaner and in shape person, Drake’s style, along with his career, has sky rocketed. Known for staying true to his hip-hop route withs slightly oversized pieces mixed with Timberland boots and the odd snapback, Drake has risen in the style ranks to make it onto our list.

drake tuxedo grammy awards mens street style
PHOTO CREDIT: Huffington Post Canada

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How to Get Drake’s Style

What Drake knows how to do best is pull off tonal looks with ease. This all black outfit works perfectly with Drakes aesthetic and style; teaming the hip-hop elements, with the baggier trousers and cap, with a sleek and fitted shirt really makes this outfit stand out, even if it is all black.

drake all black outfit mens street style
PHOTO CREDIT: HiFash Magazine

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On That Note

Of course, you may have a different list to us, but we feel that the men mentioned on this Most Stylish Men list gives you a pretty good scope on what the celebrities of this world are wearing. From Harry Styles to David Beckham, mens styles is ever changing and is malleable to whatever you want it to be. So take inspiration from one of them, or all of them, and have a go at re-creating one these looks yourself.

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