My 10 Most Stylish Men Of All Time

Michael Jackson

There is something that I always loved about Michael Jackson’s wardrobe.  Not that I would wear most of it, but his clothing was always intricately made.  I mean all of his clothes were custom.  Hey, he had the money to pay for things like that.  I think a lot of people underestimate the vision and work it takes to make his costumes and wardrobe.  They never looked that exaggerated because his normal wardrobe was very similar.  From a gold plated chest plate or that infamous crystallized glove, Michael Jackson was the man.

The Rat Pack

The style of the Rat Pack has been attempted time and time again.  That alone gives this crew of stylish friends a reason to be on my list.  Besides loving the original Ocean’s 11 and Frank Sinatra’s classic music, The Rat Pack more than anything were well-dressed gentleman (all the time).  That is the real reason why they made my list.

 Justin Timberlake

There are some people that look great in just about anything. Justin Timberlake is no exception.   The young Timberlake is one that shows how style is suppose to be effortless.  Though people pay close attention to it, the best just exude it with no thought or regard.  You can never go wrong with a suit, and to be able to perform and dance around in one and still look cool is also a plus. 

 Kanye West

Kanye has not been in the entertainment industry as long as the other members of my style list.  That goes to show you the impact he has had on men’s fashion in the last 7 years.  When he first started out as a rap artist he followed suit by saying he was the best dressed.  Some people may have looked at this as a arrogant act of self glorification, but honestly he was right.  Mr. West seems to always be 10 steps ahead of everyone.  His love for fashion has even landed him design gigs for Louis Vuitton where he had his own collection of luxury sneakers.  Kanye’s style is an important part of his image, and he is becoming a trailblazer for men’s fashion.

 Pharrell Williams

Some people like to be unconventional, and some people like to stay more conservative.  When the two are mashed up into one concoction of a man who feels reaching for the sky is limiting yourself, you get Pharrell Williams.  There are times that I would look at the outfits that Pharrell wears and it would make you think, “Who would wear that”? To me I would ask that because it sometimes seems bizarre, but that’s what makes Pharrell so righteous and cool.  To be honest it is expected if you know the type of person he is.  From a music standpoint his image reflects his music.  That is called staying true to your self, a key factor in having great style.

 Paul Newman

This is a man who finds that less is more.  Paul Newman has a certain aura about him that is fairly relative with all of us.  With his decisive picking of roles you can sort of gage what Mr. Newman likes as a man.  Newman is known for making a plain white t-shirt a staple piece that can be used frequently in many different ways. Though in real life he was not Cool Hand Luke.  He still remained one of the most cool, calm, and collected individuals I have come across in the entertainment industry.  I also find myself to be a cool mellow guy. Maybe that’s why I find inspiration through his style.

 Steven McQueen

When I think of Steven McQueen, I think of fast cars pretty women and luxurious lifestyles.  Known as “The King of Cool”, my rendition of McQueen’s life is everything I would imagine an eligible bachelor would like to live.  There is a certain dream we envision when it comes to the life of the actors we know and love.  Though in many of his movies he is perceived as swanky and well dressed, the man makes the clothes. No matter what the circumstance or atmosphere, McQueen always looked cool. I think that’s why I really like him. 

 Sydney Poitier

Actors are looked upon in society as these individuals who are trendsetters.  Thinking about the time that Sydney Poitier was popular in Hollywood were hard times for African-Americans.  Poitier was more than just an actor to the black community. He was a leader, visionary, and trendsetter.  He paved the way for many actors today.  Even one of my other picks for this list played one of his best roles (A Raisin In The Sun).  I feel I would not be doing this list justice by not putting him on it.  Hats off to you Sydney Poitier, a living legend.

 David Beckham

I truly have a love for the European lifestyle when it comes to fashion.  David Beckham is a prime example of a modern day young stylish European.  I think one of the reasons why I like his style is his influence from American culture.  It gives me something to connect with when I see what he wears and think, “I would wear that”.  His style is very edgy at times but is very classy when it comes to formal wear.  There has to be a balance of the two, and I think Beckham is a good example of that.

Sean Combs

When I think of Sean Combs, I of course cannot forget about his alter egos.  With the numerous images of the legend, it must take a man with a vision to keep up with them all.  In a way ego plays a big part in a man’s style and confidence.  Besides always looking sharp, Combs is also an entrepreneur managing an enterprise.  He is the epitome of a modern black businessman.  He has come a long way from the shinny suits.