“Angles Are Attitudes”: Men’s Style Tips From Pop Culture’s Greatest Fashion Icons

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Brooks Brothers has unveiled its new limited-edition men’s clothing line, created in collaboration with The Great Gatsby costume designer Catherine Martin. Gatsby isn’t the first pop culture project to reinvigorate interest in the distinctive and discerning man of the Roaring Twenties. The gentlemen of Boardwalk Empire and Downton Abbey have recently donned wingtip shoes, white waistcoats, and straw boaters. With the “dreamlike world of pristine green laws and lavish parties” in mind, we gathered great fashion tips from ten cultural icons to learn the secrets of sharp-dressed men.

Cary Grant

Influential style icon Cary Grant stole all the handsome during his heyday as one of Hollywood’s definitive leading men. The actor wrote a 1967 article for This Week magazine, which we spotted on GQ, discussing the finer points of men’s fashion. Here are a few of Grant’s best-dressed tips:

  • “I’ve purchased dozens of suits over the years and they all have one attribute in common: they are in the middle of fashion… In other words, the lapels are neither too wide nor too narrow, the trousers neither too tight nor too loose, the coats neither too short nor too long.”
  • “It’s better to buy one good pair of shoes than four cheap ones… The same applies to suits, so permit me to suggest you buy the best you can afford even though it means buying less.”
  • “How do I feel about ties? If I had only one to choose, then I think a black foulard, not too wide nor too narrow, is best, as it’s acceptable with most clothes. An expensive tie is not a luxury — the wrinkles fall out quicker and the knot will hold better.”
  • “Learn to dispense with accessories that don’t perform a necessary function.”
  • “Do see that your socks stay up. Nothing can spoil an otherwise well-groomed effect like sagging socks.”
  • “Don’t be a snob about the way you dress. Snobbery is only a point in time. Be tolerant and helpful to the other fellow — he is yourself yesterday.”
  • “Wear, not only your clothes, but yourself, well, with confidence. Confidence, too, is in the middle of the road, being neither aggressiveness nor timidity. Pride of new knowledge — including knowledge of clothes — continually adds to self-confidence.”

Oscar Wilde

Wilde has frequently opined about the best and worst of fashion, but in his play about the English upper crust, A Woman of No Importance, he revealed his feelings about men’s clothes through his loosely autobiographical character, Lord Illingworth: “Sentiment is all very well for the button-hole. But the essential thing for a necktie is style. A well-tied tie is the first serious step in life.”

Charles Bukowski

“I have met men in jail with style. I have met more men in jail with style than men out of jail. Style is the difference, a way of doing, a way of being done.”

Miles Davis

The jazz legend’s fashion sense was intrinsically linked to his music: innovative, seemingly effortless, hip, and daring. “An instrument should be an extension of you; it’s supposed to sound like you — the way you walk, the way you dress,” he once said. Davis always had a finger on the pulse of what was current and cool. “If you’re not keepin’ up with the times, you end up with ‘bell-bottom music,'” he advised an interviewer. “Music is the same way. I play styles… When you play styles, you’ll always be up to date, but… I won’t force one style on top of another style. It’s like wearing a sweater over a tuxedo.”

Mark Twain

Twain went topless for this 1883 photo, but the highly selective scribe didn’t advocate nudity to win top spot on all the best-dressed lists: “Clothes make the man. Naked people have little or no influence on society.”

The author’s public image was of the utmost importance to him, but he took the sentiment to new heights in his bitter attack on Czar Nicholas II in The Czar’s Soliloquy:

Clothes and title are the most potent thing, the most formidable influence, in the earth. They move the human race to willing and spontaneous respect for the judge, the general, the admiral, the bishop, the ambassador, the frivolous earl, the idiot duke, the sultan, the king, the emperor. No great title is efficient without clothes to support it.

Fred Astaire

The dapper style icon had a few tips for men that want to give ’em the old pizzazz in a 1957 interview with GQ :

  • “I’m fairly careful about tailoring.”
  • “The coat should be just long enough to cover the rear.”
  • “I just don’t like a suit to stand out. I don’t want someone looking twice at me and saying in an incredulous tone: ‘What was that?'”
  • “Be yourself — but don’t be conspicuous.”

His greatest piece of advice? “I often take a brand-new suit or hat and throw it up against the wall a few times to get that stiff, square newness out of it.”

David Bowie

Bowie’s fashion tips stem from the men he’s admired over the years. In a 1990 chat with Interview, the Thin White Duke revealed two of his earliest style inspirations that defined the original “otherworldly,” “supercool” fashions he made famous:

1961 was when I was really into clothes. I left school at 15 and started copying a bloke who used to go up on the train to London with me; Leslie, I think his name was. He was like, top mod of his own area. He wore Italian jackets with white linen jeans. Boy, was that cool! I mean, that’s in style now — it’s very much the L.A. look. But he was wearing it then, and it looked supercool. Chelsea boots, but with fluorescent pink or green socks and eye shadow that matched the socks he was wearing that day. And he had a slight bouffant hairstyle, parted in the middle. He was somehow tough-looking, too, a real heavyweight. But he had eye makeup on! And the jarringness of it was really weird. I thought, I like that — I feel that, not one thing or the other.

Former Pink Floyd frontman Syd Barrett’s androgynous style was also a major influence:

Syd Barrett was the first person in rock I had seen with makeup on. He wore black nail polish and lots of mascara and black eye shadow, and he was so mysterious. It was this androgynous thing I found absolutely fascinating. Of course, we found out later the guy had mental problems. But there was something so otherworldly about him. He was hovering, like, six inches above the ground.

Elvis Presley

Elvis was a flamboyant dresser, but he initially favored casual clothes, like denim, when he wasn’t thrusting his hips (and sideburns) on stage. Eventually he took to outrageous jumpsuits and jewel-encrusted clothing, designing many of the outfits himself. “If you’re going to be a star, you should look like one,” he once advised singer Tom Jones (who clearly took the advice to heart).

Frank Sinatra

“Cock your hat — angles are attitudes.”

Bryan Ferry

The suave glam-rock crooner has a lot to say when it comes to men’s fashion, and his love of stylish suits is no secret. In a 2011 GQ interview, Ferry — who worked at a tailor shop as a young boy — detailed the essentials of sophistication:

  • “I love the tradition of tailoring and think it is something to support. It’s like going to bookshops rather than buying something on an iPad.”
  • “English tailors are more about the construction of the suit. Italian tailors can seduce you with wonderful fabrics.”
  • “If you look at any street scene in any great black-and-white movie, every man is wearing a hat. It is a terrible shame that it now seems wildly eccentric. I wear caps a lot….”
  • “If you can afford to get two or more bow ties, I’d urge you to do it.”
  • “The great thing about black tie is that it is just a uniform. You just get one that fits. I don’t have any tricks — it’s very straightforward. I do sometimes wear a belt with black tie, which is sacrilege to most people as it’s better if you have braces. I have worn cummerbunds on occasion but they’re really out of fashion now. I don’t wear studs much — that’s my revolutionary approach.”
  • “I would rather have one great shirt than 12 that aren’t so great.”

John Waters

We’re big fans of birthday boy John Waters’ 2011 memoir, Role Models, where the Pope of Trash dispensed some great universal fashion tips:

You don’t need fashion designers when you are young. Have faith in your own bad taste. Buy the cheapest thing in your local thrift shop — the clothes that are freshly out of style with even the hippest people a few years older than you. Get on the fashion nerves of your peers, not your parents — that is the key to fashion leadership. Ill-fitting is always stylish. But be more creative — wear your clothes inside out, backward, upside down. Throw bleach in a load of colored laundry. Follow the exact opposite of the dry cleaning instructions inside the clothes that cost the most in your thrift shop. Don’t wear jewelry — stick Band-Aids on your wrists or make a necklace out of them. Wear Scotch tape on the side of your face like a bad face-life attempt. Mismatch your shoes. Best yet, do as Mink Stole used to do: go to the thrift store the day after Halloween, when the children’s trick-or-treat costumes are on sale, buy one, and wear it as your uniform of defiance.

In a 2010 interview, Waters admitted his own sense of style is rather “right-wing.” Apart from the old-fashioned “don’t wear white after labor day” rules he abides by, Waters advised that skinny jeans after 30 are a no-no and leather pants should only be worn if you’re Jim Morrison’s son.