10 Underappreciated Style Icons
Written by Charles Shoultz

By now, the most celebrated, obvious influences on classic men’s style have been picked over until their bones are white.  Everyone knows that men like Cary Grant, Steve McQueen, and John F. Kennedy are icons of male dressing, folks that any man seeking an immediate tutorial in style can learn a great deal from.  But what about the men who dressed- or dress- just as well, but haven’t received the attention they deserve?  Turns out there are lots of sharp gents who have been missing from the lists of major magazines.  Here are ten of them.

Andy Warhol: His glasses, those semi-transparent acetate frames, came to be among his more defining features, but he also ruled the roost of casual sixties cool …

Woody Allen- Throughout his long career, Allen has cultivated an image of a quintessential nerd, small and thin and nasally.  But if he is a nerd, he’s a damn well-dressed one.  Allen’s signature wardrobe of oxford-collar shirts, crewneck sweaters, and tweed sport coats is a serious study in intellectual dressing, all topped off by those iconic frames.

Gay Talese– Celebrated for his excellent writing, Talese does not always get enough attention for being a serious fashion plate.  A lover of fine clothes, his enormous, extensive wardrobe is distinctive and highly personalized, with high attention paid to details like button placement and color coordination.  It’s a dandy’s wardrobe, not for the faint of heart, but there is no better example of a man who has made his clothes completely his own.

Arthur Miller- There’s a good reason the legendary playwright was able to land Marilyn Monroe, at least for a while.  Miller, like Allen, was an intellectual, and a New Yorker to boot, both aspects of his life finding their way into his wardrobe.  He was a classic Ivy League dresser, wearing J. Press-approved three-roll-two jackets and button-collar oxford shirts.  His casual wear was perhaps more distinctive: he favored boldly patterned button-down shirts, plaids and strong stripes, short sleeve and long.

Andy Warhol- The king of pop art, the soul of sixties expressionism, Warhol wasn’t all that bad a dresser when you got to look at him.  His glasses, those semi-transparent acetate frames, came to be among his more defining features, but he also ruled the roost of casual sixties cool, with leather jackets, wide-striped t-shirts, and turtleneck sweaters.  That isn’t to say he couldn’t dress up when he wanted, but even then he would put his own stamp on it, wearing field jackets over a dress shirt and tie.

Miles Davis- It goes without saying that Miles Davis is cool.  The finest trumpet player of the 20th Century, a jazz innovator, a legend.  But his clothes were an underrated part of his appeal.  Davis was something of a chameleon, changing his wardrobe and even his hairdo as the times shifted.  He could go formal, with perfectly-fitting suits and slim ties, or he could go casual, with slouchy turtleneck sweaters and long-sleeve t-shirts.  Yet he always maintained an exacting attention to detail, leaving his stamp on his wardrobe in the color of a shirt or the shape of a jacket lapel.  Davis was at once loose and precise, like his amazing music.

Ray Charles- The king of soul music always knew how to enhance his energetic performances with a shot of sartorial power. Whether it was his sleek black suits always perfectly tailored with an immaculate white shirt and dark tie or bold patterned sport coats, sequined tuxedos and colorful sweaters, his dexterity with style was just as pronounced as his music. And it was always topped by those sunglasses, which became as much a trademark for him as his signature sound.

Bryan Ferry- Musicians have become a trend on this list, and it’s not hard to see why: with their powerful voices and heady stage presence, it shouldn’t surprise anyone that many of them are distinctive dressers.  Bryan Ferry certainly qualifies: the legendary Roxy Music frontman has always expressed himself through powerful tailored clothing, his sharp suits with their wide lapels screaming out his inescapable machismo.  It also doesn’t hurt that Ferry is an absolute master of black tie, wearing a dinner suit —and often a white or sequined dinner jacket — as though he were born in it.

Marcello Mastroianni – Long before Italian style took over the menswear scene, one of the greatest stars of the international box office was taking the suit-wearing world to school.  Marcello Mastrioanni left his stamp of indelible cool across a host of films, like 8 ½, La Dolce Vita, and Divorce Italian Style.  Mastroianni’s standout style was rooted in simplicity: dark suits, white shirts, dark glasses.  And he proves that great style is as much about how you wear your clothes as what clothes you wear.  It’s debatable if any man, even Steve McQueen, has ever looked cooler in a pair of sunglasses.

Johnny Cash- Sometimes all that’s needed to look good is a simple mantra, a rule that’s always followed, never broken.  This was something Johnny Cash lived by.  Early in his career he employed the sleek tailoring of the 1960s, but that eventually gave way to his strong-collared, loose-fitting western-meets-disco wardrobe, a rebellious style that evidenced his contempt for polite society.  And he eventually gave himself over to the darkest of colors, ensuring he would live forever as the one and only Man in Black.

Daniel Day Lewis- Lest you think all great style icons are dead or decaying, consider Daniel Day Lewis, the preeminent actor of our time.  On screen and off, he maintains the confidence and swagger of a man at ease in himself and at ease in his clothes, the basic requirement of every menswear inspiration.  We particularly love his look in the movie Nine, where he plays director Guido Contini.  Wearing the sharp tailoring of midcentury Italy, Lewis nevertheless makes his wardrobe completely his own, turning it into clothing instead of costuming.  All style icons, famous or no, have had unshakeable confidence in themselves.  This, more than any purchase that can be made or advice that can be followed, is the key to looking good.

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