Hollywood Icon James Dean's Fashionable Fingerprints Are All Over Bespoke Post's Vintage-Inspired Collab

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James Dean's legacy in film and fashion has long lived on, and a new collaboration offers the most authentic interpretation yet of the Hollywood icon's oft-imitated style.

Lovingly known as "Jimmy" to friends and family, the Brentwood-bred actor's estate has teamed with Bespoke Post on a multi-season collection of timeless menswear essentials that draw not just from Dean's onscreen wardrobes, but his inimitable offscreen life, too. The star's breakout role as Jim Stark in Rebel Without a Cause is reflected in the plain white Dean Tee and a classic red Harrington jacket by Fieldworth (Bespoke Post's in-house label), while Schott NY offers a refreshed – and equally effortless– take on the same black leather Perfecto moto jacket that Dean sported around town between filming East of Eden.

The first drop ($38-$1,525) is now available on the online menswear retailer's website and includes a Breton striped knit polo (like the one he was photographed in by pal Sanford Roth), the Barnstormer jacket, a short-sleeve raglan sweatshirt emblazoned with "Fairmont" (Dean's Indiana hometown), a gingham flannel camp collar shirt, and a honeycomb knit cotton tee in black and ivory.

There are also accessories and scents that nod to the star's farming roots and his Hollywood life. Think a silver curb chain ID bracelet by Studebaker Metals, a black leather belt with silver hardware, buffalo leather roper gloves, Ampal Creative baseball caps inspired by Dean's Prosche 550 Spyder, a tote bag, wook knit beanies, a leather- and cedarwood-infused fragrance by Boyds of Texas and a coin necklace on a sterling silver paperclip chain (price upon request) with a pendant unearthed straight from the Dean's family farm in Indiana.

More pieces will be released on Oct. 9, the day before the 70th anniversary of Dean's final film, Giant, for which he earned a posthumous Academy Award nomination.

In addition to clothing and accessories, Bespoke Post's collection features Sonic Editions archival prints ($299-$999) by photographers Allan Grant and Richard C. Miller. The black-and-white prints come in gallery-grade wood frames and show the actor on set and off duty while filming Giant in Texas.

The campaign was styled by celebrity stylist Mark Avery, whose Americana-infused aesthetic made him a natural fit for Bespoke Post's classic Hollywood-inspired collaboration. At the brand's launch party at West Hollywood's legendary Formosa Cafe, the go-to stylist for Ryan Gosling explained why Dean's style has endured, and why it still feels so accessible.

"There's honestly layers to the level in which I not only connect to the man, but the characters that he played and his influence on menswear," Avery told us at the fashionable fete. As a longtime stylist and costume designer, "James Dean's one of those guys whose picture is on every mood board. If it's not a specific shape or outfit, it's even just his vibe. He's ascended to the point where his name is an adjective. But the thing that makes his influence enduring is not just because he was obviously a beautiful person, but he embodies the spirit of starting behind the starting line."

Born on Feb. 8, 1931, in Marion, Ind., Dean lived in Brentwood for several years until his mother died of uterine cancer when he was 9. He returned to live with his aunt and uncle, Ortense and Marcus Winslow, on their farm in Indiana before returning to Los Angeles (with a brief stint in New York) to pursue acting.

Dean was 24 when he died in a car crash en route to Salinas on Sept. 30, 1955. The actor would have been 95 this year, and his estate (represented by Renaissance Licensing) is now managed by his cousin, 82-year-old Marcus Winslow, Jr., who granted Bespoke Post's creative team exclusive access to Dean's personal belongings.

Bespoke Post associate creative director Joelyn Dalit is among those who felt an instant kinship with the actor. After immigrating from the Philippines to the U.S. at the age of 10, the designer says he struggled to fit into a new culture and often felt like an outcast. And like Dean, he also rebelled against expectations – an approach that steered him towards a creative career. When he's not in New York or L.A. working in fashion, you might find Dalit riding and tending to horses on a ranch in Wyoming or surfing in Hawaii, where he went to college.

As partygoers explored the Bespoke Post pieces displayed throughout the Formosa, Dalit jokes that Dean may never have imagined that a Filipino-American man would be standing in his childhood home, reading the margin notes on his old movie scripts or gazing upon his personal collection of bullfighting memorabilia in an effort to channel his life for a fashion collection. (Dean's fascination with matadors was well-documented.)

But that's the universal appeal of his legacy; you don't have to look like the star or share his upbringing to identify with his onscreen angst or his defiance of norms, Dalit says. (Dean famously ditched the premiere of East of Eden; his method acting often alienated co-stars, and he preferred hanging out with the likes of musicians and mechanics over A-listers.)

"You did have this feeling [that] he was an outsider," says Avery of the Giant actor's move from the Heartland to Hollywood. "I think original characters and performances were who he was; there was an unspoken electricity that made you feel connected to him. Even in his performances, there was this dissatisfaction [and discomfort with] the situations that he was put in. I think all of us can relate to that, but especially people who feel underseen or feel like they don't fit in. Rebel Without a Cause is so iconic because they cast a guy who was able to embody that."

Though Jimmy died 70 years ago, his fingerprints are all over Bespoke Post's collection. Dalit notes that the limited-edition Stetson Wildcatter felt hat is finished with the actor's signature and a matador illustration. Bespoke Post director of partnerships Natalie Finch adds that details from Dean's original moto jacket (on display at the James Dean Museum in Fairmont, Ind.) were painstakingly recreated by the design team in the reimagined Schott NY Perfecto silhouette, down to the California Highway Patrol uniform-inspired waist belt and the stamped basketweave pattern.

"As much as I work with clothes and menswear, I have to say that the spirit that he breathed into that clothing is what made them special," says Avery. "The reason they were so influential was because people think, 'I wanna be him,' but part of you [feels like], 'I am him.' And that's the uniform; I wanna be associated with that guy. He was able to take the blue jeans, the white T-shirt and the red jacket and make it a symbol for something that we all understood; it doesn't matter your race, gender, age. Back then, [a white shirt] was an undergarment. By wearing it on the outside, that was a statement. It was so accessible. So many times we see somebody who looks really cool or they're able to put forward a look, but it comes with accessibility issues because things cost money."

The L.A. stylist adds, "Dean took things that you could buy at Sears and he put it together in a way that created a character and sent a message. For me, that's why I was always attracted to workwear. [Growing up in Virginia], I could afford style, but I couldn't afford fashion."

For Dalit, connecting with Dean's legacy also reinforced his own creativity and passions, many of which might be considered analog hobbies in today's social media age. He points out the actor's wide-ranging pursuits beyond acting, from riding motorcycles and sculpting to playing the bongo drums and sports. It's that creative spirit that Bespoke Post also hopes to inspire in wearers.

Of course, the brand's Hollywood-worthy collection wouldn't be worth adding to cart without the seal of approval of someone who knew the star best. Winslow was just 11 when Dean died and was like a younger brother to the star, who nicknamed him "Markie." He still lives on the family's farm in Indiana, and Finch shares that he was left in tears after seeing the finished pieces.

The James Dean Museum in Indiana will host the 50th annual James Dean Festival from Sept. 25-27. The three-day celebration will include a look-a-like contest, a parade, a '50s fashion show, live music, local vendors, carnival rides and a car show.

Here in L.A., Griffith Observatory will pay homage to Dean with screenings of Rebel Without a Cause on Oct. 5 and 26. (The landmark starred in the 1955 film and is home to a bronze bust of the actor.) On the big screen, Dean will (sorta) be seen in filmmaker Guy Guido's upcoming biopic based on William Bast's memoir, Surviving James Dean, per The Hollywood Reporter. True Detective star Brandon Flynn will play the late legend in Willie and Jimmy Dean, which will center on the duo's romantic relationship in the 1950s.

Shop the first drop of the Bespoke Post x James Dean collection online here, and mark your cal for the second release landing on Oct. 9.