I’ve seen a few  ‘Best dressed men’ list and while I agree with many of the selections, I personally would rather view a list of ‘Style influencers’.  Me being who I am I decided to put together a list of some of the chaps I consider the greatest style influencers, gentlemen who I believe exemplify Casual Fly.  The names are in no particular order and while they are of different eras they share a few common threads - These men do not have stylists (at least not to my knowledge), and dressing seems to be an obvious extension of who they are while also being reflective of the individual (not who they wish they could be).

For those of you who follow the site you know that I take fashion with a grain of salt and that I believe that style is something that comes naturally and is developed over time.

"To attain style in dress you must look perfectly happy and relaxed in your clothes which must appear part of you rather than a wardrobe you have donned." ABC of Men’s Fashion page 108, By Hardy Amies.

Guerreisms’ Presents The Style Influencers (Part 1)

Miles Davis (Jazz musician)

Regarded as one of the most innovative, influential and respected figures in the history of music.  Not only was Miles ahead of most in terms of Jazz, his manner of dress showed a man who did not follow trends but instead created them.  Miles would combine elements, add his experience and personalty and make the style uniquely his. 

He began his professional career wearing second hand Brooks Brothers suits from a pawn shop a few years later Miles would be wearing, according to Down Beat, “what the well dressed man will wear next year.”  He was not one to stick to one style, instead he constantly reinvented himself from the Ivy League Look to Slim cut European suits to having his jackets cut specifically for his slouchy playing posture.

This man learned the rules, then rewrote them.

Frank Sinatra (singer)

The man that rocked the fedora with ease, class and cool.  Sinatra exuded a calm cool second to none. Tailor made suits and tuxedos were signature pieces of Sinatra.  There was no confusing things when looking at Sinatra, this chap could sing, dress, party and enjoy life … and did it all in a great suit!

Frank Sinatra is one of those rare gentlemen that could rock a bow tie or a loose tie with an unbuttoned top button and still looked comfortable and good in any situation.  A suit didn’t make him look good, he certainly made the suit look great.

GIanni Agnelli (Founder of Fiat)

Esquire Magazine named him one of the five best dressed men in the history of the world - that in itself says plenty.  His style was classic Italian which was common (he was born and raised in Italy) but it is he who exemplified Sprezzatura.  He would often wear his watch over his cuff, or wear high brown boots under a bespoke suit.  He understood and knew the rules of style before changing them.  It is precisely his knowledge of the fundamentals of style that allowed him to break the rules… rewrite the rules in a way that very few could and still can copy without looking foolish and forced.

Gianni immaculate in dress and the little details he included made his style completely his.

Nickname: “The Rake of the Riviera”

The Duke of Windsor (King Edward VIII)

At 5’5”  The Duke of Windsor understood the importance of the right items and fit.  His jacket waists were cut precisely to elongate his silhouette.  He always carried a cigarette case and all the pockets on the left side of his trousers were cut wider for that reason.  The duke of Windsor although a short man gave the impression of being taller because he understood how to play with patterns that would normally be a no go for small people.

The Duke of Windsor was master of bespoke suits.  Paying attention to every detail he believed in clothing that lasted a lifetime and the right fit.  His wardrobe extended some 60 years because he never lost his slim figure (his waist remained between 29 and 31 inches). 

This gentleman exemplified impeccable dressing and set the tone for the smoking jacket, the Windsor knot, and shirts with Windsor collar.

Andre Benjamin (Andre 3000)


His style exemplifies re-invention and the evolution of self, from Hip Hop kid to cultivated style.  At a time when hip hop ‘style’ was ‘cool’ he traveled the road less popular and while looking back at some of his early style photos, it is evident that as he explored (without fear) he was able to find a style that was completely his own.  Mastering colors and patterns, Andre 3000 brought cool to Preppy while transforming Preppy into a new style.  He understood inner city urban and uptown classic and mixed the two doing it in a way that only he could.

Andre 3000 is one of those chaps that oozes style and knows how to dress down something loud with his personality.  With him bold isn’t too much and even if it’s too much for your subdued taste, you can’t help but acknowledge that he pulls it off effortlessly.

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(Source: Guerreisms.com)

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