Best Dressed Male TV & Movie Characters

Posted by Rishi Chullani on

Alyssa Breeden

From an early age we have been exposed to influential and powerful men on television, and whether we realize it or not, they have helped shape who we have become – and what we would like to become. Clothing has a powerful way of addressing who we are and opens a small umbrella of our beliefs as soon as we walk through a door.

Not sure if you follow?  Here are some examples of the best dressed male TV & movie characters in history – only the dapper ones, of course.

Boardwalk Empire

Boardwalk Empire Men's Style

The year is 1920 and the tailoring is impeccable.  Blood stained bespoke?  You know these guys are gangsters from the start, before a word is spoken. Set in Atlantic City, these guys wanted it to be known that they are equals with the “big guys” in the surrounding large cities.   There is a seriousness about this crew that can only be captured with tailor-made looks and details.

To me, the best part about this series is that these costumes are authentic to the period in which they’re from; even the fabric choices were authentic. Most notable is Nucky (Steve Buscemi), based on a real “top notch dresser” – who, much like his character is portrayed, wanted it to be known when he presented himself to the public. Everything about this character’s clothing lets you know that he is a man in charge.

James Bond (Over the Years)

James Bond Style

James Bond, the ultimate playboy – it kind of feels synonymous with the bowtie.  I don’t think it’s an accident that this character always resembles Hugh Hefner.  Always surrounded by beautiful women, James Bond makes wearing a suit look badass.

This designer knew exactly how to portray Bond. What woman can resist a bad boy who is always dressed to the nines?  It does make you wonder:  how does he get that much movement in those suits without popping seams?  It seems as though we all need extra spandex gussets before “trying this at home”.

Mad Men (Don Draper)

Don Draper Style

How could there be a best-dressed fictional character list that doesn’t mention Don Draper?  I mean, come on, this guy keeps fresh pressed dress shirts in his office drawer. 

Never straying from his signature look, Don Draper is the absolute epitome of the mid-century executive.  Secretive and successful, a lack of color and sleek lines speak to his secretive personality.

Kingsman Secret Service

Kingsman Secret Service Men's Style

More spies in suits!  If nothing else is gathered from this piece, we can all agree that the costumers for these productions use suits to portray professionalism, status and seriousness. 

Set in London, this film screams Savile Row. The Kingsmen are literally named after a tailor shop, so of course they are coming out top notch for every occasion. Take note that these guys are also investigating high-end cases and mingling with the 1%, they have to play the part.  This film is a perfect implementation of impeccable tailoring, beautiful suiting, and perfectly tied knots.

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Empire (Lucious Lyon)

Empire Lucious Lyon Style

Empire Entertainment, the top of the hip-hop world in this series.  Of course the men in this office are going to be presented as upper class and dressed professionally, yet you will notice that they still appear very approachable.  Specifically, Lucious Lyon – who presents himself much like a southern Baptist preacher.  Who wouldn’t trust a Baptist preacher?  A depiction that seems wildly appropriate since his character is trying to wash away his past sins.

Imagine yourself walking into a studio about to sign your life away to a record label, now think of the person that you would want to see on the other end of the table.  An image of Lucious Lyon may appear if you didn’t know any better.  This is why you never see the character presented too intensely.  He’s sharp but not rigid.  Stuffy monochromatic schemes are never seen on Lyon for good reason.

The Great Gatsby

Great Gatsby Style

(Gatsby in pale colors, clearly not “having it all”.)

Jay Gatsby, who doesn’t love Gatsby?  With the allure of the roaring 20's, beautiful beads and a lack of morals – what’s not to love? 

In this story, Gatsby is almost presented as a God-like figure, always appearing in light, floating colors – he’s as high as society gets.  He’s clean and pure, or at least that’s what he wants you to believe.  Gatsby is almost appears like a dream in pale colored linen and seersucker – a glutton and sharp dresser, Gatsby seems to have it all. 

The Wolf Of Wall Street (Jordan Belfort)

Wolf Of Wall St Style

Another film portraying successful businessmen, The Wolf of Wall Street gives you a glimpse of how to portray your worth through the use of clothing.  These characters start off in cheap suits and wrinkled shirts as they are trying to find their place, but throughout the duration of the film you can see the transformation to tailor made Italian suits as the money starts coming in. 

The person to focus on here is DiCaprio, he never lets his image slip – even when he is literally slipping onto the ground from his high society car.  DiCaprio’s looks are dictated by what’s happening in the scenes: want to make DiCaprio look more powerful while controlling the crowd?  Red.  Party man DiCaprio?  No jacket and a sleeve roll (think pool party scene).  This film shows exactly how easy it is to transform from stuffy businessman to party boy with a simple sleeve roll.  Take notes on this character...but not too many! 

Better Call Saul (Howard’s character – always dressed on point)

Better Call Saul Style

Is he a good guy or a bad guy?  His arrogance, in both his personality and wardrobe, make it a bit hard to tell. 

Better Call Saul is set in the 2000's, yet Howard has a collar bar – power move.  Never showing too much personality and keeping it safe (color-wise), Howard’s character can be hard to read.  It seems as though the show’s followers never really grasped how to feel about this guy and I think the wardrobe knew exactly how to make it such.

American Psycho (Patrick Bateman)

American Psycho Patrick Bateman Style

A well-dressed, handsome…serial killer.  It’s perfect. 

Bespoke suits keep Bateman looking powerful and put together.  No one would ever suspect the beautiful man in the expensive, tailored suits to be a horrible person...right?  However, be sure to note the pops of red in Bateman’s wardrobe, red suggests power – but also a bit of danger.  There seems to be bits of red all over each of his costumes, even in his playful suspenders.  Not sure what I mean?  Just go back to the opening credits.

Crazy Stupid Love

Crazy Stupid Love Style

This film really drives home the idea that sometimes clothes really do make the man.  In this film Carell’s character has lost everything, including himself.  He must start over and rebuild his life.

This film sends an obvious message:  sometimes all it takes is a little wardrobe revamp to rebuild your confidence.  Revamping his style, really taking into consideration every piece, reveals a whole new character.  If you want life to take you seriously, dress the part.

Not sure how you feel about this idea?  Take the time to watch Crazy Stupid Love.  Have you ever seen a bad movie involving Michael Scott?  I didn’t think so. 

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Ocean’s Eleven

Ocean's Eleven Men's Style

The con artist, the ultimate societal chameleon.  When you’re planning to heist a casino you have already dedicated your mindset to “go big or go home”. These guys knew how to play the game; if you want to win big you need to look the part.  Inconspicuous.  (Think about the scene where Pitt reveals himself as a doctor.)

You will notice a lot of relaxed looks in this film.  “Off-duty”, if you will.  It reminds the watcher that these are regular guys with regular lives.  Though as the plot thickens, something about the way that these guys present themselves makes you realize that something isn’t quite right.  Yet, every look is executed precisely. The power of accessories and details reveals itself.

Reservoir Dogs

Reservoir Dogs Men's Style

Reservoir Dogs is a great example of the “not so undercover” mobster look.  Everyone knows that a group of men in black suits, with no added color what so ever, literally mean business.  Men in Black, anyone?

The interesting part of this film, however, is that these men were given colorful names to keep their real identities blurred. When giving a description of the men, you would only notice that they all look the same - an ideal situation for a group of criminals.  It is a strong look, a powerful look.  The black suit, crisp white shirt and black skinny tie look is normally reserved for the most formal situations – however, these guys are wearing them to kick ass.  This film speaks loudly to power and shows the simple versatility and total masculinity of the black tie look.

Wall Street

Wall Street Men's Style

It is apparent that Wall Street always has, and always will, have its own unspoken dress code.  Look rich, think rich.  Look trustworthy, but not too soft.  It’s the Wall Street way. Ties required but never too tight – cheap suit?  Must be bad at your job.  Show them you mean “business”. 

That’s exactly what’s going on in this film.  Yeah, it’s the 80's but there are no cheesy hammer pants and shoulder pads here.  These guys want to be taken as seriously as their money stealing schemes.


Goodfellas Men's Style

To me, Goodfellas is the quintessential mob movie – I know, I know the Godfather.  In this film, these men come dressed for success, success with taking your head for crossing them. 

A personal favorite because the mindset is that because these men are dressed in power suits, it is obvious that they are not playing any games.  On the other hand, there is also a professional innocence associated with being so well dressed. “That guy doesn’t look like a criminal”, as I have mentioned several times throughout this article.  That’s what they want you to think, and why the mobster look is so perfect.  Snapping necks without so much as wrinkling their suits. Flawless. 

Another thing that should be pointed out about this film is that these are Italian men in mid-century America, crooners were well loved and still all the rage.  There was definitely a certain suave associated with this look and they took it and ran.

And that's a wrap for this one! We hope that you have enjoyed reading this as much as we have writing it!

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