The 20th century has seen literally hundreds of changes in the evolution of men’s style. We’ve seen top hats, bell bottoms, parachute pants, skinny jeans, skinny ties, Nehru jackets, hip huggers, flannel suits, leather jackets, tuxedos, dinner jackets, Zubaz pants, polyester leisure suits, flannel shirts, zoot suits, jean jackets and 4,763 different hats worn by Stevie Wonder, Andre Benjamin, and Mr. Francis Albert Sinatra himself.

We at Manner acknowledge these style changes that have taken place throughout the years and have taken it upon ourselves to name who we think represent the epitome of style for each decade throughout 20th century. While this is not an exhaustive list of the men who have inspired and become icons of fashion and style for millions of men around the world, we feel that if ever there was a Mount Rushmore of men’s style, these men would definitely have their faces on the mountain.

Teddy Roosevelt, 1900-1909

TR comes up a lot whenever people get to naming the all-time greatest presidents Though quite possibly the manliest man not named Steve McQueen to ever live, Old Rough and Ready was also a hell of a dresser, whether in his white battle gear worn during the Battle of San Juan Hill, or in this number, complete with pocket watch and chain.

George “Babe” Ruth, 1910-19

The Great Bambino. The Sultan of Swat. When you think “baseball,” it inevitably conjures of images of this legendary slugger, still lauded by many as the greatest hitter of all time. What escapes most is, as one of the richest men in America during his time with the Yankees’ legendary “Murderers Row,” George Herman Ruth was a hell of a dresser. This made him a celebrated playboy of his era, so much so that on several occasions, he was placed on the DL due to The Clap. Sultan if Swat, indeed.

Tie: Rene Lacoste & F. Scott Fitzgerald 1920-29

This one was hard for us to choose only one. One was any Ivy League-educated writer who penned possibly the most stylish and influential American novel of all time. The other was a tennis legend who literally invented the polo shirt (Lacoste’s nickname on the court was “The Crocodile,” if you ever wondered why your shirts had that emblazoned on its breast.)

F. Scott Fitzgerald and his wife, Zelda, embodied the lifestyle and dress of the Gilded Age and was able to paint The Great Gatsby as colorfully and as flamboyant so much so that before we ever saw a film adaption of the novel, we saw Gatsby in our minds and were able to experience the hollow decadence of the Roaring 20s. Rene Lacoste essentially turned tennis into the game it is today, proving to be an artist both at center court and off of it.

Errol Flynn, 1930-39

“I’ve had a hell of a lot of fun and I’ve enjoyed every minute of it.”

Any man to utter those words is sure to have few regrets while laying upon his deathbed. Errol Flynn was, by many accounts, the most celebrated playboy of old Hollywood, and perhaps of all time (the phrase “In Like Flynn” isn’t bestowed upon one who’s bad with the ladies, gents.)

Not only was Flynn one of the greatest Lotharios ever, but he was a legendary carouser. A common guest at newspaper magnate William Randolph Hearst’s mansion parties, Flynn was often thrown out for severe intoxication. While that is part of what led to an early death in 1959 at the age of 50, it did nothing to end the legend of the Australian swashbuckler who even today is held up as the paragon of action stars in film. It’s also worth mentioning that Flynn made it into not just one, but TWO Dylan songs. Now THAT is a legacy.

Humphrey Bogart, 1940-49

He wasn’t handsome. He wasn’t tall. He wasn’t particularly smooth or debonair. But for a relatively brief time, Bogey was The Man. He single-handedly embodied the role of the antihero and the film noir genre of film in such all=time classics as The Maltese Falcon and The Big Sleep. We’d be remiss of course if we failed to mentioned his role in Casablanca, and how the man fucking OWNED the white dinner jacket. Maybe that’s a big part of how he was able to snag Lauren Bacall, possibly the most beautiful woman in Hollywood history.

Cary Grant, 1950-59

The name “Archibald Leach” isn’t the most glamorous sounding name on the planet. It sounds like the name of an 1840s gold prospector, or maybe a close friend of Montgomery Burns. It doesn’t sound like the name of one of cinema’s most celebrated leading man of all time, but the man christened “Archibald” was to become the Cary Grant. Yes, that Cary Grant. The man who made North by Northwest the most stylish thriller of all time. The man who never wore a suit. The suit was, in fact, a part of him; there was no distinction between the two.

Muhammad Ali, 1960-69

His mama named him Clay…I’mma call him Clay

He was an Olympic Gold Medalist. A political icon. A rabble rouser. A traitor. A Civil Rights giant. A provocateur. Sports Illustrated’s Greatest Athlete of the 20th Century. But above all, he was The Champ. Louisville’s native son. And when he wasn’t wearing a pair of gloves and boxing trunks, Ali cut one hell of a figure in a suit. This decade may have been the toughest of all for us to choose just one man to represent a decade so full of sartorial diversity and experimentation, but we figured we couldn’t go wrong picking the man who made boxing AND getting dressed so elegant and so effortless. The Champ may no longer be here, but his legacy in and out of the ring will remain eternally untouchable.

Mick Jagger, 1970-79

Honorable mention: Former Jagger lover and certified alien David Bowie.

Prince, 1980-89

Dearly beloved…We are gathered hear to present our choice for the most stylish man of the 1980s. This was another tough choice, but we ended up going with the man who arguably defined the exaggerated fashion of the decade and also loomed over his peers with a talent unequal before or sense. While The Purple One may not cut the traditional, masculine figure like that of Cart Grant, Rock Hudson, or George Clooney, we never got bored of Prince and the outfits he wore. He was always thinking 127 steps ahead, muscially and sartorially, which is why he has always been the vanguard of rock n’ roll style. And while he is missed dearly, his presence has never left us and his influence will prove to bear fruit for decades to come.

Lenny Kravitz, 1990-99

So it’s come down to just one man, and, while we laboured over our choice for most stylish man of the last decade of the century, Lenny won out over a field of very qualified gentlemen. Our knee-jerks were Clooney, or Pretty Boy Pitt. We were even considering English rock n’ roller Jarvis Cocker for a while.

But when it came down to it, one man stood out and clearly embodied the decade in both style and body of work. Lenny Kravitz was a GIANT in the 90s, and to this day, few people look more like a rock star than he does on a regular basis. This is why when we wrote a piece on The Most Stylish Musicians of the 90s last year, Lenny was on the list. I give you Exhibit A:

So…there you have it, gang. The ten giants of men’s style of the last century. Some we’re easier to pick than others, and some are sure to get some jeers and spark debate. We’re interested in hearing YOUR picks and what we got completely wrong. We look forward to the hate mail. You can also follow us on Twitter and check us out on Instagram @manner4men. To see some of our other style article, visit our homepage. -Eds.