How To Make Good On The Bad-Boy Look

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How To Make Good On The Bad-Boy Look

Words by Henry Duffield

Four hours ago

Left: Marlon Brando in 1950. Photograph by John Engstead/John Kobal Foundation/Getty Images. Right: Steve McQueen on the set of “The Great Escape” (1963). Photograph by Mirisch/United Artists/Album

Few things shaped the trajectory of menswear quite like the advent of the Hollywood bad boy. Through the likes of Marlon Brando and James Dean, the newly defined teenager of 1950s America was inspired to wear a T-shirt instead of a sack suit and jeans in place of slacks. The world had a new set of rules after the war, and kids were excited to break them.

Over the 20th century, rebellion would take on many styles. Much of what was once seen as defiant is now a staple of any man’s wardrobe, but some just don’t suit everyone.

Take the leather jacket. Initially designed for motorbike riders and fighter pilots, they became the ultimate signal of ruggedness and adventure. Why is it, then, that so many men struggle to pull them off today? What separates the style of the rebel and why do others miss the mark?

The renegade’s look has never been an accident. Its history tells us much about how to wear it.

01. Workwear as an act of rebellion

In the early 1950s, kids across the West spilled out of movie theatres with a new idea of cool. The high-waisted slacks and point-collar shirts of the older generation were out. T-shirts and jeans were in.

The T-shirt had long been an undergarment, first issued to members of the US Navy, then adopted by the working class, as a barrier between skin and uniform. Similarly, the five-pocket jean had become the reliable choice for miners, factory workers and farmers; denim was sturdy and light, while rivets reinforced points of stress. But when Brando wore his fitted tee as Stanley Kowalski in 1951’s A Streetcar Named Desire, the status of the garment changed overnight.

The role was complicated, brutish, but undeniably masculine, and young people were gripped by the power of a T-shirt and bare arms. Brando would return to the screen in 1953 as motorbike-riding gangster Johnny Strabler in The Wild One, this time teaming his T-shirt with a Schott Perfecto leather jacket and blue jeans, spurring another rebellious shock wave.

The Perfecto jacket was banned from schools; T-shirts and hair grease became essential street style. Jeans transcended blue-collar settings and, in both the Soviet Union and Japan, were traded on black markets. Their utility – the image of a young man whose life is far too wild for slacks and a sweater – was the transgression, and that’s what made them cool.

02. The reappropriation of military uniform

WWI saw planes with open cockpits fly higher and faster than ever before, exposing pilots to temperatures as low as -55°C, prompting the design of the warm shearling bomber jackets. As cockpits were made warmer, they became smaller and enclosed, requiring jackets with greater mobility. Enter the A-2 and MA-1 bombers, which cropped at the waist and allowed room for elbow and shoulder movement.

On the seas, naval seamen were fitted with flared-leg pants, which could be rolled up when water was on deck. On the frontlines, soldiers were issued various field jackets, the most popular being the M-65, heavily associated with the Vietnam war.

When their respective conflicts ended, these garments returned home on the soldiers who wore them and as surplus supplies donated to charity shops. For the rebels of the 1960s, this was a new uniform.

Anti-Vietnam war protestors bought up the flared pants and bomber jackets, reclaiming the military clothes as a form of protest. The flared pants would then become a style cue for the 1970s, while the jackets would have iconic moments in Hollywood. Steve McQueen wore a brown leather A-2 jacket in 1963’s The Great Escape, while Robert De Niro was menacing in his M-65 in Taxi Driver (1976).

The MA-1 bomber would be popular among young British men through the 1970s. It’s also the model bomber jackets are designed after today.

The garments were not only utilitarian, they were also affordable, with a distinct establishment association the youth wanted to oppose. Like workwear, the engineered military garments brought together function and mythology: a recipe for the rebel’s uniform.

03. Play the sporting field

The tribalism of sport was a natural environment for renegade belonging and opposition, shaping how they dressed. Sneakers were a breakthrough in sportswear in the early 20th century. Over time, they transitioned from something worn on the court to a lifestyle, and as Tommy Ramone said, “it was punky and snotty to wear sneakers instead of shoes”. By the late 1980s, the rise of hip-hop had sneaker culture dominating footwear.

One of the upper class’s favourite sports, golf, also ultimately styled the rebel. The Harrington jacket was made for the mobility required of a golf swing, cropped at the waist and wide through the body. Despite perfectly representing the image of conformity, the Harrington became a favourite of the rebel, as worn by James Dean in 1955’s Rebel Without A Cause and Elvis Presley in King Creole (1958), as well as subcultures including punk, mods and rockers all the way through to the 1990s.

Polo shirts, sweats, hoodies, baseball caps – there is no end to the impact sportswear had on youth cultures. They all point to one thing: for the rebel, there is no line between work and play.

04. The secret to wearing a leather jacket

Tracing the rebel’s style history, a pattern emerges – everything was designed for a purpose that wasn’t just about looking good. The T-shirt was underwear. The bomber jacket was engineered for dogfights. The sneaker was for a basketball court. The leather jacket offered protection.

This is not a history of fashion; it’s about clothes. Clothes protect your knees from the asphalt. They keep you warm in an open cockpit at 25,000ft. They hide your sweat on a first date and cut through the wind on a London street corner at night. The rebel ignores fashion – the force that tells us what to wear – because they love their clothes.

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown