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How to Dress Like James Dean

An icon for the youth of 1950s America, James Dean’s style was incredibly simple and yet, has remained the benchmark for the art of dressing casually decades later. Best remembered for his star-making turn as disaffected Jim Stark in Rebel Without a Cause, the casual cool of James Dean is something that many strive for.  

The confidence and effortless, stylish swagger from the bad-boy of the silver screen provide many lessons for those editing their wardrobes. His was a timeless way of dressing and one that you can easily replicate. Should you want to, here’s how to dress like the iconic James Dean.  

The Simple White T 

James Dean was one of the style figureheads that made the white tee-shirt so iconic. Underestimating the humble tee would be your first mistake. A simple silhouette and a good cut, it’s a definitive menswear garment that will never fall out of style and can be worn with anything.  

Select a size that is slim to the body but not restricting. James wore his with Levi’s 501 denim, featuring a straight leg cut and a high rise, as well as tough leather boots with minimal detailing for a practical and timeless look.  

Classic White V-Neck T-Shirt

Size:S

$58

Boxer Pocket T-shirt White

Size:S

$58

Boxer Pocket T-Shirt Navy

Size:S

$58

&SONS Essentials Vest

Size:S

$45

The Jacket 

Dean was known for throwing on a lightweight jacket. These casual jackets were common as work and casual wear back in the day, worn with everything from day to night outfits. The real head-turner and the one we most likely know him for was the iconic red jacket from “Rebel Without a Cause”. Apart from the vibrant red shade, James Dean’s blouson was actually rather unassuming, it was the way he wore them that made him a boss. He held himself with a huge amount of self-assurance and the confidence he had in himself bled through to his clothes and you can’t help but think, that “cool” doesn’t even cut it when describing him. 

If you want to channel “Rebel Without a Cause”, choose his iconic ensemble of red Harrington jacket, white T-shirt, jeans, and boots. Choose to imitate Dean directly by getting one in bright red, or opt for other colours like beige, burgundy, or navy for more versatile options. 

Rebel Harrington Jacket Red

Size:S

$248

Rebel Harrington Jacket Blue

Size:S

$248

RYDER Hardwear Canvas Jacket

Size:S

$248

The Polo 

If you ever doubted the Polo as a vital piece for a Pioneer’s wardrobe then perhaps Dean’s style will prove it for us.  

On the set of his final film, Giant, James Dean became friends with photographer Sanford Roth. Sanford and his wife Beulah became almost adoptive parents to Dean, frequently hosting the actor at their Los Angeles home.

During one of these visits in the summer of 1955, Roth pulled out his camera and snapped some candid photos of the actor revealing a more sensitive side, looking both playful and philosophical.

Roth often brought out his camera when Dean was visiting, capturing the actor in a variety of poses and outfits, though the most famous of these spontaneous sessions featured Dean in a unique Breton-striped top complete with Johnny collar. The ultimate classic piece, paired with jeans and boots - you can't go wrong.

&SONS Breton Knit Navy

Size:S

$147

&SONS Alberto Polo

Size:S

$128

The Leather Belt

Accessories can be uncharted territory for many men but almost all styles can be elevated with the addition of a leather belt.

Loop it around, and your look will instantly come together because this accessory is a mark of self-assurance in your silhouette (something that Dean had in bucket loads). Pair with jeans and a buttoned club shirt like the man himself.

Virgil Thin Tan Leather Belt

Size:S/M

$58

Club Shirt Navy

Size:S

$121

The New Frontier 14oz Selvedge Anti-bac Raw Denim Jeans

Size:30

$229

Brandon Jeans Charcoal

Size:30

$159

Club Shirt Grey

Size:S

$121

Black Leather Belt

Size:S/M

$83

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