On the Road: Sam Riley Channels Kerouac in Dark Blue Flannel Plaid

Sam Riley as Sal Paradise in On the Road

Sam Riley as Sal Paradise, Jack Kerouac’s alter ego, in On the Road (2012)


Sam Riley as Sal Paradise, aspiring writer based on future Beat icon Jack Kerouac

Queens, New York, Winter 1947

Film: On the Road
Release Date: October 12, 2012
Director: Walter Salles
Costume Designer: Danny Glicker

WARNING! Spoilers ahead!


Jack Kerouac was born 100 years ago today on March 12, 1922 in Lowell, Massachusetts. His 1957 roman à clef On the Road became a defining work of what would be called the Beat Generation, chronicling the author’s wanderings in the late 1940s with contemporaries like William S. Burroughs, Neal Cassady, and Allen Ginsberg, all thinly disguised in the novel with pseudonyms.

Kerouac had started work on the novel almost immediately upon returning from his travels, the original draft being a continuous, single-spaced 120-page “scroll” that he typed across three weeks in April 1951. This free-flowing stream of consciousness has been called the ideal medium that captured the mad impulses that drove his adventures with Cassady, represented by the larger-than-life character Dean Moriarty.

Published six years later, On the Novel launched Kerouac to literary stardom and invited decades of ongoing analysis, criticism, and influence across all artistic mediums. Despite its fame, On the Road resisted cinematic adaptation for more than half a century, though Kerouac himself had shown interest in bringing it to the screen as indicated by a letter he sent to Marlon Brando the same year that the book was published, suggesting that Brando play Dean while Kerouac portray his own alter ego, Sal Paradise. (While Kerouac’s acting skills remain untested, the kinetic character of Dean Moriarty does seem a suitable fit for Brando’s particular talents.)

Francis Ford Coppola purchased the rights to On the Road in 1979, a decade after Kerouac’s death, but the project languished in development hell for decades as Coppola himself struggled to write a script. After seeing The Motorcycle Diaries, Coppola tapped director Walter Salles and writer José Rivera to bring the novel to the screen. Years of research and rewriting led to a script that blended elements from Kerouac’s original scroll with the fictionalized pieces of the final novel, with filming finally commencing across the latter half of 2010 across various locations in Canada, the United States, and even briefly in the Andes.

Éric Gautier’s cinematography felt like one of the movie’s strongest aspects, beautifully capturing the parts of the continent that have changed little in the three quarters of a century since Kerouac and Cassady’s cross-country treks: the nature, the small towns, and the road itself.

Responses to On the Road were mixed, and perhaps the novel’s own “unfilmable” nature is what doomed production for all these years. That pulsating, unpredictable energy so embodied by Kerouac’s writing and his literary portrait of Dean Moriarty can never be truly replicated by a movie, a medium that relies on substantial planning and always some degree of artifice and intentionality.

That said, Garrett Hedlund’s performance as the impulsive Dean remains another strong aspect of the movie—as it should be—as Hedlund captures the bedeviling charisma and rootlessness that would have made him a fun companion for adventures… and unreliable when it’s time to go home. Given his significance as the chassis for these adventures, it’s appropriate that the movie begins with the same four words that Kerouac used to launch Sal’s narration:

I first met Dean…

What’d He Wear?

On the Road introduces us to Sam Riley as Sal Paradise, hunched over his typewriter in Queens in a haze of writer’s block of Camel smoke. He’s dressed in a blue plaid flannel shirt, one of at least five that he would cycle through over the course of the movie, establishing a loose “uniform” for our author surrogate. Sal’s on-screen garb includes a rotation of at least twenty shirts, mostly long-sleeved work shirts in variously weighted flannel cloth, with the occasional sweater.

The limited selections available to Sal in his “road closet”, typically hefted around the country in a Army-style rucksack, requires pieces both versatile and durable enough to withstand the rigors of the road… and of a friendship with the unpredictable Dean Moriarty. In addition to a few military items like his olive “jeep sweater” and G.I. khakis, most of what Riley wears as Sal echoes the sturdy workwear that had been increasingly popular during these postwar years and were a fixture of the real Jack Kerouac’s wardrobe. (The third chapter of On the Road even includes a “wool plaid shirt” fished from Sal’s canvas road bag and lent to a fellow wanderer named Eddie, with Sal mourning the loss of the shirt—and its attached sentimental value—when the absent-minded Eddie hops into a passing trailer.)

“[Kerouac was] swayed by the rugged look of Americana,” wrote Brenden Gallagher for Grailed. “It was the style of the lumberjack, the farmer, the factory worker, the painter and the military man that moved him. He combined these working class looks with the bohemian flavor of the beatniks to create what writers in the years after would call ‘anti-fashion’; today we would likely chalk this look up as ‘street style.’ While Ginsberg was known to sport a thrift store blazer and a second-hand tie, Kerouac looked every bit the part of the Americana wanderer. Together, they helped create a defining look in American counterculture. More specifically, Kerouac’s style was at once a homage to, and identification with, the American working class.”

Jack Kerouac

The real Jack Kerouac, clad in his characteristic plaid flannel work shirt, in the 1950s.

Costume designer Danny Glicker wisely selected to source some of Sal’s shirts through a partnership with Pendleton Woolen Mills, the venerated Portland-based outfitter known for their wool board shirts and blankets. Several of Riley’s screen-worn shirts have the obvious characteristics of a Pendleton board shirt—such as the woven loop collar and the dual pockets with non-buttoned flaps—but I’m not sure if this first flannel was one of the Pendleton pieces.

The shirt’s pattern reflects a simple dark blue-and-white buffalo plaid as its foundation, overlaid with a gradient-shadowed blue double-lined grid check. The cloth is a heavy flannel wool, a smart layer for keeping warm while spending long wintry nights perched at a typewriter next to his bedroom window.

Sam Riley as Sal Paradise in On the Road

The shirt has a comfortably large fit, consistent with the era’s fuller-fitting style that Sal accentuates via his practice of often wearing his shirts only partially buttoned—if at all—in this case, leaving all the dark blue 4-hole buttons undone on the plain front with its horizontal buttonholes, always showing his undershirt. Sal’s white ribbed cotton sleeveless undershirts have higher and more rounded necks than the typical A-shirt (or “wifebeater”, to use the unfortunate nickname these undershirts obtained around the same time as his travels with Dean.)

Kristen Stewart and Sam Riley in On the Road

Impressed by her ability to roll a joint, Sal stops to talk with Dean’s underaged wife Marylou (Kristen Stewart). The cinematic version of Marylou makes a stronger impression on Sal than her literary counterpart, whom he describes from their first meeting as “awfully dumb and capable of doing horrible things… outside of being a sweet little girl.”

Sal’s wide collar lays flat, with a short loop-tab made from the same cloth extending from the left side, presumably to fasten to a smaller button positioned under the right collar leaf. The shirt has two chest pockets, but—unlike the traditional Pendleton board shirt—these are open-top pockets with no flaps. The sleeves end with a buttoned cuff, though Sal keeps these undone and rolled up his forearms.

Sam Riley as Sal Paradise in On the Road

Chad King (Patrick John Costello) tells Sal and Carlo Marx (Tom Sturridge) about his wild friend Dean, newly arrived from Denver. Though Hal Chase—who inspired the Chad character—introduced Neal Cassady to the Beat circle, Chase would soon distance himself from the group, particularly after William Burroughs shot and killed his common-law wife Joan Vollmer in 1951. Marx was Kerouac’s nom de plume for Allen Ginsberg.

Sal wears taupe-brown wool trousers, likely pleated, with side pockets, jetted back pockets, and turn-ups (cuffs) on the bottoms.

While on the road, Sal hits the pavement in a pair of worn-in brown leather derby-laced work boots, and these heavy-soled brown shoes he wears during these early scenes in New York appear to be the same. These boots would be a smarter choice for the road than the Mexican huaraches that Kerouac described in the first part of the novel as “plantlike sieves not fit for the rainy night of America and the raw road night,” further criticized by his fellow traveler Montana Slim and forcing Sal to ponder why he brought “the silliest shoes in America,” which had since been reduced to “bits of colored leather sticking up like pieces of a fresh pineapple.”

Sam Riley as Sal Paradise in On the Road

For a night on the town, Sal pulls on a red and black buffalo check flannel work jacket. Often associated with lumberjacks, this check pattern was developed in the mid-19th century by a designer at Woolrich in central Pennsylvania. The pattern caught on among outdoorsmen, and “Woolrich jacket” emerged as a shorthand term for these rugged red-and-black jackets, whether they were actually made by the company or not.

In fact, Woolrich’s current lineup—as of March 2022—doesn’t quite include the same sort of zip-up, four-pocket buffalo plaid jackets as worn in On the Road, but you can still find a few from other companies like the Legendary Whitetails Men’s Outdoorsman Jacket (Amazon).

Sam Riley as Sal Paradise in On the Road

“I went to the cold-water flat with the boys, and Dean came to the door in his shorts.” — On the Road, Chapter 1

Such a blue-collar garment would seem out of place on the streets of cosmopolitan New York in the late ’40s, but this aligns with the sartorial statement that Kerouac and his fellow Beats were perhaps unintentionally making, as argued by G. Bruce Boyer for MR PORTER (and quoted by Gallagher in Grailed):

“Hip” was the youthful point of view that emerged after WWII, as a counterweight to both the fear and conformity of a bleak past and a dubious future. Prole clothes and a laid-back demeanor formed its aesthetic correlative. The angry young rebels in the 1950s were the precursors of the new way fashion would work: not from the top of the social ladder down, but from the bottom up. Street clothes and work clothes—the gear of cowboys and ex-GIs, industrial laborers, the zoot suits of the jazz musicians that Mr. Kerouac adored, and farm hands—would enter the realm of style. It was the style of the Underclass Hero, the Prole Rebel.

This waist-length jacket zips up from the waist hem to the neck, at the crux of the wide-pointed shirt-style collar. Two patch pockets are rigged at mid-chest, each covered with a flap that closes through a large black button. A gently slanted hand pocket is set-in on each hip, just below the chest pockets. The set-in sleeves are finished with a pointed cuff that closes through a single button, and a short tab on each side of the waist can adjust the fit.

Sam Riley as Sal Paradise in On the Road

While Carlo Marx and Chad King have adopted more city-friendly overcoats, Sal dresses for the New York City nightlife in his buffalo check work jacket when he’s taken to his destiny via an introduction to Dean Moriarty.

How to Get the Look

Sam Riley as Sal Paradise in On the Road

Sam Riley as Sal Paradise, Jack Kerouac’s alter ego, in On the Road (2012)

Jack Kerouac dressed consistently with his working-class roots, scrabbling a closet full of military surplus gear and heritage workwear brands like Pendleton and Woolrich for an understated style now associated with countercultural toughness: a mid-century rebellion against the idealized conformity of “the man in the gray flannel suit” represented by men in dyed flannel shirts instead, worn with practical work jackets and boots instead of chesterfields and oxfords.

  • Blue-on-white shadow plaid woolen flannel long-sleeved shirt with camp collar (and loop), plain front, two chest pockets, and button cuffs
  • Red-and-black buffalo check woolen flannel zip-up waist-length hunting jacket with button-down flapped chest pockets, slanted hand pockets, and side-adjuster waist-tabs
  • Taupe-brown wool pleated trousers with belt loops and turn-ups/cuffs
  • Brown leather derby-laced work boots
  • Black socks
  • White ribbed cotton sleeveless undershirt

Do Yourself a Favor and…

Check out the movie, and read Kerouac’s 1957 novel: both the published version and the author’s “original scroll” are available.

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