Mad Men: Roger Sterling’s First Navy Blazer (and LSD Trip)

John Slattery as Roger Sterling on Mad Men. (Episode 5.06: "Far Away Places")

John Slattery as Roger Sterling on Mad Men. (Episode 5.06: “Far Away Places”)


John Slattery as Roger Sterling, Madison Avenue ad executive

New York City, Fall 1966

Series: Mad Men
Episode: “Far Away Places” (Episode 5.06)
Air Date: April 22, 2012
Director: Scott Hornbacher
Creator: Matthew Weiner
Costume Designer: Janie Bryant


Tomorrow may have a storied association with cannabis, but today—April 19—has been deemed “Bicycle Day”, recognizing that wild Monday night in 1943 when Swiss chemist Albert Hofmann recognized the highly potent psychoactive properties of LSD during a mind-bending bicycle ride home from his Basel lab.

Hofmann had first synthesized lysergic acid diethylamide five years earlier but his experience on April 19, 1943 now considered the first LSD trip in history. In re-synthesizing the product, Hofmann accidentally ingested 250 micrograms, leading to an intense and ultimately “not unpleasant intoxicated-like condition” for several hours. The experience convinced Hofmann of LSD’s power as a psychiatric tool, never imagining that it would be used recreationally. While Hofmann’s initial hypothesis was correct, with psychiatric patients like Cary Grant benefiting from the power of the drug, Timothy Leary’s experimentation with LSD brought the drug to mainstream consciousness, and acid trips became inextricably linked with the zeitgeist of the swingin’ ’60s.

Appropriately, it was during Mad Men‘s often-experimental fifth season, set from 1966 into 1967, that we get some extended time with characters experimenting with drugs. As with many Mad Men episodes, the sixth episode “Far Away Places” refers to a popular song of the era, though few of the characters physically transport themselves any further than upstate New York. In fact, our true New Yorker Roger Sterling doesn’t even leave Manhattan, bringing his trophy wife Jane (Peyton List) to a dinner party that surprisingly ends in an LSD trip that becomes not only a highlight of the episode but of the series as a whole, scored in part by The Beach Boys’ “I Just Wasn’t Made for These Times”.

The California band’s landmark album Pet Sounds had only been released three months before the episode’s setting in early September 1966, and the song addresses Roger’s struggle with the looming threat of irrelevancy and his ongoing search for youth. Roger’s life-changing LSD encounter refreshes him more than any love affair with a PYT ever could, changing his course from spiraling insecurities to eventual contentment.

Of course, it’s an ad that significantly speaks to our conflicted Madison Avenue man during his first trip, featuring Ted Knight promoting the invigorating “Great Day for Men” hair dye. Knight was a bit-part actor and commercial voice artist at the time he posed for that Great Day ad in 1966 and—like Roger Sterling—Knight’s greatest days were still ahead of him such via his Emmy-winning performance on The Mary Tyler Moore Show and his role in the iconic comedy Caddyshack.

John Slattery as Roger Sterling on Mad Men

His mind expanded during his inaugural LSD trip, Roger Sterling ultimately gives up his desperate quest for youth and—like Ted Knight, featured in the hair dye ads—would undergo a more organic renaissance as he progresses through middle age.

What’d He Wear?

“Far Away Places” marks the start of a whole new Roger Sterling, beginning a chapter replacing Lucky Strikes with LSD and supplanting business suits with blue blazers and boots. While Roger’s signature three-piece suits would stay in regular rotation through his mustached swan song in the finale, the blue blazer became a late-series staple in his wardrobe, ranging from this traditional navy single-breasted blazer to the bright marine-hued double-breasted jackets he would wear in the final season.

John Slattery and Peyton List on Mad Men

When Roger Sterling steps into the elevator in his super-trad navy blazer, white shirt, and tie, he looks far from the type of man about to experiment with drugs… and yet, the blue blazer signals a sartorial gateway to his own relaxed fashions and mindset in the years to follow.

We had already seen Roger in the occasional sports coat during off-hours, but he debuts his first of several navy blazers for this life-changing dinner party. This particular jacket is the most traditional style of blazer, made from a dark navy wool and single-breasted with two gilt shank buttons on the front matching the trio bedecking each cuff. Roger neatly folds his white linen pocket square into three peaks pointing up from his welted breast pocket. Accented with sporty swelled edges, the blazer’s notch lapels are moderately wider, perhaps signaling Roger’s willingness to follow the expanding fashion trends… as well as expanding his mind.

Roger’s bright scarlet red silk tie still leans toward the skinny side, tied in a tight four-in-hand and detailed with orange crowns that echo Roger’s princely self-image. The tie’s narrow width may make the crowns appear to be haphazardly scattered, but they are actually organized diagonally as though positioned along “downhill”-direction stripes.

John Slattery and Peyton List on Mad Men

The happy couple.

Most of the men at Sterling Cooper Draper Pryce still wore primarily white dress shirts at the time, though while Don Draper preferred a rigid “uniform” of French-cuffed shirts, Roger characteristically favored shirts with less fussy button cuffs, rakishly adorned with his monogram. In this case, the left cuff of his white cotton poplin shirt has been embroidered “R.H.S.” in burgundy thread that echoes his tie.

John Slattery and Peyton List on Mad Men

We don’t see Roger’s shoes on screen during this sequence, but he’s almost certainly wearing the black calf semi-brogue oxfords that were his usual footwear throughout the fifth season, both in and out of the office, before he would become a full-time devotee of more mod ankle boots. Also unseen—but likely still worn—is one of Roger’s black leather belts with an “S” etched somewhere on the silver buckle.

One of my favorite aspects of this outfit are Roger’s trousers. I’ve always preferred gray trousers with blazers over khakis, and Roger takes this classic look to the next level with his twill flat front trousers patterned with a subtle dark pinstripe, either dark navy or black. When he’s seated, Roger’s plain-hemmed trouser bottoms break higher over his dark cotton lisle socks.

John Slattery as Roger Sterling on Mad Men

“My name is Roger Sterling. I have taken LSD. I live at 31 E. 66th St. New York, New York. PLEASE HELP ME.”

Roger wears an ornately detailed gold class ring on his left pinky with a black-filled tonneau face with the regal insignia from his high school, represented only as “PHS”. Each side of the ring commemorates 1927 as the year of Roger’s graduation from the mysterious institution.

John Slattery as Roger Sterling on Mad Men

Interestingly, it’s the hand with his high school class ring—recalling his youthful heyday—that Roger uses to cover the white-haired side of the hair dye ad that so significantly impacts him during his LSD trip.

For someone born into money and happy to live the carefree of a privileged playboy, the Tudor Oyster Prince may be the most aptly named wristwatch for Roger Sterling. Beginning with the fifth season, series property master Ellen Freund worked with vintage watch specialist Derek Dier to re-dress the wrists of the major characters, with a 1959 Tudor ref. 7967 chosen for the cheeky ad man. Roger’s Tudor was one of a set of four Mad Men-worn watches that was auctioned by Christie’s in 2015 alongside Megan Draper’s Jules Jorgensen, Pete Campbell’s vintage Hamilton, and Don’s luxurious Omega DeVille.

Strapped to Roger’s right wrist via black leather bracelet, the Tudor’s stainless steel case is an elegant 33mm in diameter, small by today’s standards, enclosing a silver-ringed black gloss “tuxedo” dial with luminous hands and powered by a 26-jewel automatic movement.

John Slattery and Peyton List on Mad Men

After a mid-trip bath that transports Roger to the infamous 1919 World Series, he and Jane dry off in silk robes and pink turbans as they lay on the floor and come to terms with their failed relationship.

John Slattery and Peyton List on Mad Men

All it takes is Roger and Jane’s most authentic moment of intimacy to realize that their relationship is effectively over.

What to Imbibe

Sure, anyone can crack a bottle of Stolichnaya, but—for the full Roger-on-LSD experience—you’ll need a bottle of Stoli that fills the room with the Red Army Choir singing “The Song of the Volga Boatmen” every time you unscrew the cap.

John Slattery as Roger Sterling on Mad Men

Эй, ухнем!

Stolichnaya debuted on Mad Men during the third season premiere, “Out of Town”, when Roger returns from his and Jane’s honeymoon bearing gifts for Don:

I have Stolichnaya and Cuban cigars. I sent them from Greece.

The episode is set in spring 1963, years before Stoli became the first Russian vodka to be legally imported to the United States, adding context to the suggestion that Roger had to package up his contraband and also cultivated a connection that would keep his office bar well-stocked with Stoli, customs laws be damned. According to Brands and Films, SPI Group partner Andrey Skurikhin collaborated with the Mad Men team when they contacted him about the placement, even lending the production team a vintage bottle from 1963.

Brands & Films continues to say that Stolichnaya had started making inroads to American sales in 1965 when it appeared at select retail locations in Brooklyn, giving Roger—and the dinner party hosts—less hoops to jump through in order to stock their respective bars with the Russian state-owned vodka. Under Nixon’s détente policies of the early ’70s, PepsiCo struck a groundbreaking deal with the Soviet government that permitted exportation of Pepsi into Russia in exchange for the rights to market and more widely sell Stoli in the United States.

How to Get the Look

John Slattery as Roger Sterling on Mad Men. (Episode 5.06: "Far Away Places")

John Slattery as Roger Sterling on Mad Men. (Episode 5.06: “Far Away Places”)

Roger Sterling’s navy blazer, white shirt, and red tie may scream trad, but the outfit sartorially signifies the emergence of a new Roger who’s more prepared to authentically experience life rather than yearning for the appearance of foregone youth.

  • Navy wool single-breasted blazer with swelled-edge notch lapels, two gilt buttons, welted breast pocket, hip pockets, 3-button cuffs, and double vents
  • White cotton poplin shirt with spread collar, front placket, and single-button cuffs (with burgundy-embroidered monogrammed left cuff)
  • Scarlet red silk skinny tie with orange crown motif
  • Gray dark-pinstripe woolen twill flat front trousers with belt loops, side pockets, and plain-hemmed bottoms
  • Black leather belt with monogrammed silver belt buckle
  • Black calf leather semi-brogue cap-toe oxford shoes
  • Black cotton lisle socks
  • Tudor Oyster Prince (ref. 7967) watch with steel case and black-and-white “tuxedo” dial on black leather strap
  • Gold class ring with black filling

Do Yourself a Favor and…

Check out the series.

The Quote

You always say I never take you anywhere.

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