“James Dean crafted an individual style for himself which has lasted the test of time: a youthful look in a classic white T-shirt, a cropped jacket and worn-in blue jeans.” --Vogue

The year: 1955. The film: Rebel Without a Cause. The icon: James Dean. And the outfit: blue jeans, a red jacket, and a slick white T-shirt.

There’s no look quite as iconic. For every rebellious teen in the 50s, dark and brooding Jim Stark, portrayed by Dean, was the picture of cool. And if you wanted to imitate his style, you knew the T-shirt was the basic that laid the foundation for his whole look.

So how did the Classic T-shirt become synonymous with effortless cool? Dean had a lot to do with it. Let’s break it down.

Related: The Evolution of the Classic T-Shirt

How the T-shirt became the rebel’s go-to garment

James Dean solidified the T-shirt’s reputation as the go-to garment for rebels, but he wasn't the first start to make the T-shirt famous. He took his cue from Marlon Brando, whose signature look centered around a plain white T-shirt in A Streetcar Named Desire.

Back in the time of Brando and Dean, the T-shirt was considered an undergarment. To wear it on its own made a statement. By disregarding the commonly held ideas about how a T-shirt could be worn, those who wore T-shirts by themselves were rule-breakers. 

Pair that sentiment with the rules-be-damned attitude of Dean’s Jim Stark, and you have the recipe for an easy rebellious style. But it wasn’t just what Jim Stark aspired to be that people loved, it was how they could relate to who he was at his core. Prior to the 1950s it was a bit rare to see American actors playing authentic characters on the screen, because Hollywood was all about the hero, good vs. evil, and holding actors and characters to high, perhaps unrealistic and strict standards.

That reflected expectations of American culture of the time, and pushed rebelliousness to the shadows. While Hollywood was known for glamor, the stage was known to be where “real” actors developed, and when those actors transitioned to the screen, they carried an unprecedented element of authenticity with them.

Enter Marlon Brando, who changed filmscape forever with the 1951 adaptation of Tennessee Williams’s A Streetcar Named Desire.

HOW BRANDO USED A WHITE T-SHIRT TO BRING OUT THE DARK SIDE OF STAN KOWALSKI

Unlike many films of its time, the leading man in A Streetcar Named Desire is not at all a role model, and that was what made Brando’s portrayal of Stanley Kowalski such an iconic performance. Often seen lumbering around the house in nothing but an undershirt, Kowalski is anything but the Southern gentleman the esteemed Blanche DuBois expects him to be. It’s his house, his rules, and challengers should not expect him to play nice. 

While the character Kowalksi is despicable, Brando’s performance is worth admiring in that he brought authenticity from theater to film. Viewers were so captivated by his performance because they could relate to Kowalski and all his flaws--almost making him an anti-villain of sorts. This paved the way for the ultimate anti-hero: Jim Stark

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A REBEL WITHOUT A CAUSE CHANGES THE T-SHIRT

Whereas Brando made the T-shirt about embracing our dark side, James Dean made the T-shirt about overcoming it. Whereas it was more typical to portray an All-American protagonist as more of a heroic do-gooder, Jim is just a guy on a quest to find himself, and he’s being held back by the controlling nature of his mother and society. The troubled teen character was not only relatable, but inspiring. 

“Dean's famous costume in Rebel Without a Cause – the red blouson jacket, Lee jeans, white T-shirt and that perfect quiff – was designed to reflect what the 50s newly defined teenager was wearing” --The Guardian 

Unlike Kowalski who just does what he wants and doesn’t try to change himself, Jim tries his best to do the right thing in spite of who he is. Jim doesn’t hide his dark side or try to smooth out his edges, but he does fight to become the best man he can be, and he tries to inspire others to rise to the occasion. 

The T-shirt became more than just a symbol of rebellion, but also hope. As many people of James Dean’s generation challenged rules and expectations, the T-shirt became a symbol of a new beginning. One of raw authenticity, unapologetic honesty, and coming of age. 

The influence of Dean’s style is apparent in countless actors from John Travolta to Hugh Jackman who followed in his footsteps, and the next generation showed us being cool and coming of age doesn’t mean you can’t have a little fun along the way.

THE T-SHIRT BECOMES A TIMELESS CLASSIC

Grease took things a step further in the 1978 classic Grease. Borrowing from Dean’s classic cool, John Travolta brought vibrancy and nostalgia together to solidify the T-shirt as a timeless classic. It wasn’t just about being cool, it was fun, expressive, energetic and catchy. 

With classics like Summer Lovin’ and Grease Lightnin’ that played on repeat in the heads of many fans, so too did the images of tough guys who could dance--the T-shirt was not just a classic throwback, but a symbol of redefining masculinity. Travolta showed that men could be cool and expressive at the same time, all while subduing arrogance with an unassuming plain white T-shirt. 

From there, T-shirts became a staple in and out of movies. It’s hard to imagine a movie where the hero doesn’t wear a T-shirt… but even when you suit up like James Bond, you still want something to keep you cool and comfortable underneath.

Related: How to rock a suit with a V-neck T-shirt

Beyond Jim Stark,THE T-SHIRT TAKES OFF

James Dean’s influence as an actor wasn’t the only way he helped the T-shirt take off. Off screen, Dean was known for rocking a simple style. Beyond his days as Jim Stark, why did James Dean himself favor the simple T-shirt?

Many believe it reflected his love of simplicity. Dean, who grew up on a farm in Marion, Indiana, had a rough-around-the-edges genuineness that other stars of his time lacked. He didn’t cast away his style in favor of Hollywood glitz and glam. Instead, he stuck true to his roots and made simple cool, even in an industry that revolved around flashiness.

The public took notice. Simple looks, like jeans and a T-shirt, done confidently became a kind of high fashion for the underdog. The signature look for those who strayed off the beaten path. A style symbol for those who didn’t care about fitting in.

WHO HAS JAMES DEAN’S LOOK INSPIRED?

The Legacy lives on modern celebrities who have embraced minimalism and simplicity as the new pillars of the Gentleman's fashion. Rather than going for showy suits and attention grabbing shirts the subdued simplicity gives you a clean look that accentuates your masculine features in a more authentic relaxed way. We’ve highlighted a few celebrities whose style provides plenty of inspiration

Blake Griffin

On the court, Blake Griffin is a force to be reckoned with. Off the court, Griffin knows how to tone it down with simple fashion that makes him seem friendly, approachable, and casual but classy. Taller guys always do well to keep it simple. Your height already calls a lot of attention to you, so a solid color high quality T-shirt conveys quiet confidence… especially when you find yourself in a roast battle with Jeff Ross. 

Hugh Jackman

The man who plays Wolverine can look pretty rough around the edges, but a high quality well fitted T-shirt really cleans up the look. By wearing well-fitted T-shirts, Jackman is able to subtly draw attention to his figure, and the plain color and high quality element are a great contrast to his natural scruff and the refined roughness that we see in characters like Wolverine. As himself, Jackman comes off as approachable, powerful, and stylish with a plain T-shirt.

Shawn Mendes

For some, it’s all about keeping up boyish good looks, and Shawn Mendes knows how to let a T-shirt bring out his bright and fun side. With a wide grin and lively expression, Mendes turns Dean’s “tortured teenage style” on its head. Sometimes a T-shirt helps you embrace your younger side--the unassuming plain white T-shirt is like a canvas you can use to paint your personality into your style.

James Franco

Known for casual outings and having a laid-back work style, James Franco is known for wearing graphic tees, sometimes featuring none other than himself. While the Classic T-shirt doesn’t offer graphic tees at this time, we like how James Franco wears T-shirts to get down to business but without taking himself too seriously. 

Related: how to wear a T-shirt at work

How to channel James Dean’s cool

It's pretty obvious that the days where a T-shirt is considered only an undergarment are long gone. But that doesn’t mean you can’t make a statement by dressing simply. In fact, there are whole Pinterest boards dedicated on how to chicly style a simple T-shirt.

The beauty of the Classic T-shirt: by making it the foundation of your look, you can let something else shine. Maybe it’s a personality-packed accessory. Maybe it’s a bold blazer. Or maybe, like it was for James Dean, it’s your inner cool.

But in order to create a look like James Dean’s, you need to make sure you’re choosing the right T-shirt.

What to look for in a T-shirt

Not any old packaged T-shirt will do if you're building a fashionable look. For style that looks cool and not cheap, you need to pay attention to your shirt’s fit and fabric.

When choosing a fit, the first thing to consider is your shirt’s cut. Do you want to opt for the classic crew cut, or go for a more plunging V-neck?

Classic Crew Cut T-shirts feature a round circular neck. They provide excellent flexibility in that they can be worn as undergarments or standalone pieces.

V-neck T-shirts have necklines shaped like the letter V. They work well to accentuate or slim down your physique.

For more details, check out our complete T-shirt style guides for men and women 

Once you’ve settled on a style, be sure the T-shirt you’re choosing is one that will fit well. Does it drape in a way that flatters? If you’re shopping online, check the reviews and see what past purchasers are saying about how their order fits. Keep an eye out, too, for what reviewers say about how the shirt holds up in the wash.

And lastly, you want to choose quality fabric. Cheap T-shirts might be fine for hitting the gym, but when it comes to making a fashion statement, only the best quality T-shirts will do. Aim for super soft, organic cotton to avoid a starchy feel and stiff look.

Related: Follow these tips to find high quality T-shirts

Luxury T-shirts for James Dean-inspired looks

Attractive drapes, clean necklines, and seamless finishes. That’s what you get when you choose a Classic T-shirt. It’s the perfect foundation for a look that’s James Dean cool.

Each Classic T-shirt is made with 100% organic, super soft cotton that’s garment-dyed, pre-washed, and pre-shrunk. They’ll look great wash after wash—you won’t have to worry about shrinking or shape-shifting.

Better yet, all of our cotton is sustainably sourced and free from pesticides and GMOs, and all of our shirts are hand-embroidered with fair trade labor.

That means you won’t just look good, you’ll be doing good. And that’s a kind of coolness that never goes out of style.

Find your next style staple today by browsing our collection of men’s T-shirts (or women’s T-shirts—ladies can definitely find inspiration for style from James Dean too, learn more about how women have helped pioneer the T-shirt in our T-shirt guide for women).

Related: Are expensive luxury T-shirts really worth it?