Jon Hamm as Don Draper, former ad man in search of himself
“Somewhere in California”, Fall 1970
Series: Mad Men
Episode: “Person to Person” (Episode 7.14)
Air Date: May 17, 2015
Director: Matthew Weiner
Creator: Matthew Weiner
Costume Designer: Janie Bryant
WARNING! Spoilers ahead!
Five years ago today, Mad Men‘s final episode “Person to Person” aired on AMC, concluding a decade’s worth of storytelling as we followed advertising director Don Draper (Jon Hamm) and his family and colleagues as they navigated the tumultuous 1960s.
Few could have anticipated when the pilot episode aired that the confident Madison Avenue hot shot’s corner office domain would be reduced to a lonely corner of a Big Sur retreat by decade’s end, yet it makes sense that his lifelong pattern of retreat—of running away from anything undesirable, be it a poverty-stricken childhood of abuse, the horrors of war, or a dishonest marriage—would find the erstwhile Dick Whitman pushed as far as he can go, from one coast to another until he finds his last refuge at a literal retreat. To continue “moving forward” in Don’s own parlance would mean dropping off of Carmel’s storied cliffs and into the ocean, paralleling his likeness “falling” through the series’ iconic Saul Bass-inspired opening credits… of course, just as Don constantly assures us—and himself—that everything will be okay, that falling figure in the credits always lands back on the couch, looking self-assured and in control with a cigarette in hand.
At the start of the final half-season, Don’s colleague and one-time professional rival Ted Chaough (Kevin Rahm) had pitched him on the premise that “there are three women in every man’s life.” Don first scoffs at the seemingly tired trope, but the finale finds the once-aloof ad man striving to make “person-to-person” connections with his trio: his teenage daughter Sally (Kiernan Shipka), his ex-wife Betty (January Jones), and—finally—his trusted protégé Peggy Olson (Elisabeth Moss).
When we had first met each of these women in 1960, they were almost completely reliant on Don. Now, checking in with them at the start of the next decade, they have completely eclipsed his influence with Sally maturing into an independent young woman, Betty sadly left to the uncontrollable fate of her advanced lung cancer, and Peggy at the helm of her own professional ambition. Don’s latest attempts to find a woman to “rescue”—Diana (Elizabeth Reaser) and Stephanie (Caity Lotz)—have both failed and, his natural inclination to retreat no longer an option, he can barely save himself. Hardly a shell of the confident creative director who developed Lucky Strike’s winning advertising strategy on the fly, Don’s final call to Peggy is ostensibly to make up for the fact that he didn’t get a chance to say goodbye.
“I know you get sick of things and then you run, but… you can come home,” assures Peggy, but Don resists the suggestion, unable to fulfill it not only due to the lack of rides leaving the retreat over the next few days but also the fact that he has no real home to return to…
I messed everything up. I’m not the man you think I am… I broke all my vows, I scandalized my child, I took another man’s name and made nothing of it.
The call is a heartbreaking catharsis for Don and sets Peggy off on her own emotional roller coaster when her subsequent call with Stan Rizzo (Jay R. Ferguson) leads to the free-spirited art director declaring his own love for her, establishing her likelihood of a happy ending balancing professional and personal fulfillment on her own terms.
But… back to Don, who—as communicated by Jon Hamm’s bravura performance—falls into a powerful nervous breakdown at Big Sur. Anyone familiar with suicidal ideation recognizes where his mind is and his own weak assurance that he’s “in a crowd” to wave off Peggy’s reasonable suggestion that he not be alone, ending the call before she could break through his self-reinforced spiraling depression. He sits prone with only his Penney’s bag—the remnants of his life—beside him. Indeed, all that’s left of the man that was once Don Draper has been reduced to a few pieces of clothing in a shopping bag. The penthouse furniture moved out, the business wardrobe and lucrative career abandoned, and his luxury car given away. At the end of “The Milk and Honey Route” (Episode 7.13), it seemed like freedom for the newly rechristened Dick Whitman to be rid of these belongings, but now this minimalist existence makes it all the more easier for him to throw it—and thus his own life—away.
It feels like that may be the next and final step for Dick, until the airy Sheila (Helen Slater) arrives to take him to his next seminar and thus in the relative but temporary safety of a “crowd” that he assured Peggy would keep him safe. The suggestion is a self-fulfilling prophecy as Don finds himself emotionally moved by a seemingly bland fellow guest named Leonard whose account of his own perceived invisibility allows Don to forge a genuine, authentic person-to-person connection with another human. For once, he truly isn’t alone and thus… he is finally safe.
One particular review of the finale that particularly resonated with me was scribed by John Teti of the ever-exceptional The AV Club, presenting a far more articulate tribute to a top-notch concluding hour for one of my favorite shows. As Teti masterfully describes the scene:
The monologue has Don’s rapt attention as he hears from a kindred spirit—someone else who’s isolated not by their failure to give love but by their inability to receive it.
Don is the opposite of Leonard in some ways. Leonard laments how uninteresting he is, while Don is used to being the center of attention when he walks into a room. But their fundamental pain is the same. Leonard describes a dream of being on a refrigerator shelf. He’s aware that there’s a party going on outside, a joy that he can see in the smiles of people who open the door and look in on him. But they never pick him to join the party. Leonard’s vision is a permutation of Don’s purgatory, in which Don is surrounded by tantalizing images of a happy, fulfilled life and maddened by the impossibility of making them real. Like Leonard, Don can describe the happiness that he envisions—in fact, he’s built a career out of describing it—he just can’t sample it for himself.
Don faltered in that first exercise, when he was asked to wordlessly show his feelings toward another person in the room, but now he can’t hold himself back. He wraps his arms around Leonard and sobs, an unspoken show of gratitude for someone who shares his fundamental struggle to connect.
Don’s emotional connection provides the viewer with a brief sense of comfort that allows the show to break away and present vignettes of how the rest of Mad Men world is being sent off into the seventies: Pete and Trudy Campbell, reconciled and beginning a new life in Wichita… a fiercely independent Joan Holloway-Harris kicking off what promises to be a successful self-owned business… a rakish, retired Roger Sterling living la belle vie with Marie Calvet, having finally found a partner appropriate both in age and temperament… Sally Draper, forced into the role of caretaker for her younger siblings and her own mother, who continues to defiantly blow smoke in the face of her fatal lung cancer diagnosis… and Peggy and Stan, working late but together. We see that everyone will be fine, at least for now… but what about Don Draper?
The final diegetic shot of the series pans across the Big Sur coast at dawn to Don, sitting barefoot, cross-legged, and content among a crowd practicing sun salutations as the leader promises “a new day, new ideas… a new you.”
What’d He Wear?
Audiences watched Don Draper complete his journey from the archetypal “man in the gray flannel suit” to the man in the plaid flannel shirt, a transformation that may have shocked viewers initially attracted to the show’s well-tailored mid-century business suits. Despite this sartorial shift, Janie Bryant’s acclaimed costume design neatly suits the Don we’re seeing in this moment: stripped down to his roots, a son of rural Pennsylvania dressed in the rugged garb long associated with its hardworking denizens.
Don may have always needed his finely tailored gray worsted suits for work at the office, but he has his hardest work ahead of him—emotional growth—and needs to be dressed appropriately. Despite cyclical appropriation by the counter-cultural set of the moment (in the ’90s, grunge; by the late 2000s, hipsters), plaid flannel shirts have been a staple of rural laborers since at least 1850 when Woolrich Woolen Mills in Pennsylvania borrowed the Scottish “Rob Roy” plaid and rechristened it “buffalo check” when marketing these distinctive red-and-black woolen shirts to local lumberjacks. (You can read more about this history from Stitch Fix.) More than a century later, titans like Carhartt and Pendleton had entered the game and plaid flannel in various tartans and colorways was going mainstream thanks to stars like Marilyn Monroe… who was decidedly not a lumberjack. Still, these hard-wearing shirts maintained their association with rugged outdoorsmen.
Until this episode, Don Draper had never so sartorially connected with his roots, dressing even for the occasional manual labor in outfits like an open brown linen button-up with khakis and loafers as seen in “Marriage of Figaro” (Episode 1.03). Even while traversing the country in “The Milk and Honey Route” (Episode 7.13), the previous episode, his plaid shirt was more of a sports shirt that wouldn’t look totally out of place in a Manhattan executive’s weekend wardrobe.
But now, clad in flannel shirt, jeans, and work boots, Don has reverted to Dick Whitman, back at the same crossroad he had faced decades earlier with the choice to determine if he will begin his new life again with deception and the power of convincing appearances… or with emotional openness and honesty that encourages genuine growth.
Don’s shirt is patterned in a brown, aqua blue, and off-white tartan plaid cotton flannel twill, with a point collar, two patch pockets with mitred corners, and button cuffs that he wears undone and rolled up his forearms. All seven buttons up the front are a slightly lighter brown four-hole sew-through plastic.
In their infinite wisdom, Mad Men superfans and style experts Tom and Lorenzo noted the significance of Don’s blue and brown shirt:
Don’s breakdown—this time; because he’s had about a half-dozen in the last ten years—was partially spurred on by his fascination with Diana, who notably wore two different uniforms when we first met her, one in pale blue and one in brown. That color combo has haunted Don and hung over this season, repeating again and again. When he couldn’t rescue Diana, he turned to Stephanie, another mother who abandoned her child, and transferred all his energy to her. When she bolted from his weirdly obsessive attention and bad advice (“Oh, Dick. I don’t think you’re right about that.”) he turned to another woman who gave her child up [Peggy]…
Don has never looked more modern than he does right here. This costume could be put on a man his age in 2015 and not look odd. That’s also not insignificant, since he’s about to have a breakthrough moment that will propel him out of his past and into the present and future.
Don’s dark blue stonewash denim Levi’s 501 jeans are the same as he had worn with his Levi’s trucker jacket at the start of the episode. These “Original Fit” jeans are essentially unchanged since Levi Strauss & Co. modernized the 501® in 1947, though they can be identified as post-1964 jeans due to alignment of the belt loop along the back of the center seat seam. According to the ScreenBid auction that followed the end of series production, Don’s jeans were sized 36×33.
Don wears his jeans with a thick dark brown leather belt that closes through a large squared brass single-prong buckle.
Don wears dirty dark brown leather plain-toe work boots, derby-laced through three sets of brass eyelets with three brass speed hooks up the ankle-high shaft. They are typical combat-inspired work boots of the era, similar to what was offered by the venerated Minnesota-based shoemaker Red Wing during the 1960s as these vintage examples from Red Wing Amsterdam and Prairie La Crosse illustrate. In fact, Don’s boots are one set of eyelets shy of being nearly identical to the currently offered Red Wing Heritage Blacksmith 6-inch boot in copper “rough and tough” leather (available via Amazon and Red Wing).
The boots have tan contrast stitching and hard dark brown leather soles. His tall black socks are likely the same Gold Toe socks he’s been wearing throughout his cross-country travels.
He may have given up his Cadillac and his penthouse apartment, but we can’t blame Don for holding onto his classic Omega Seamaster DeVille, the same luxury watch he had started wearing at the start of the fifth season. Mad Men property master Ellen Freund worked with vintage watch specialist Derek Dier to select the period-correct timepieces for the series, including this Omega that Christie’s auctioned for $11,875 in December 2015.
The Christie’s listing describes the watch as “Signed Omega, Automatic, Seamaster, De Ville, Ref. 166.020, Movement No. 23’943’081, Circa 1960.” It has a slim steel 34mm case, a black cross-hair dial with a date window at 3:00, and is worn on a textured black leather strap.
By episode’s end, Dick Whitman has made his decision; rather than beginning his new life in another man’s uniform and restarting his maddening cycle of dishonesty, he is barefoot, clad only in a clean white shirt and crisp khakis, a vulnerable outfit but one symbolizing his readiness to begin his new life with a clean slate.
How to Get the Look
For some, Don Draper may present his most accessible (and comfortable) outfit to date in the closing half of the series finale, dressing for his existential despair and depression at Big Sur in a plaid flannel shirt, jeans, and work boots.
- Brown, blue, and off-white tartan plaid cotton flannel twill work shirt with point collar, front placket, two patch chest pockets, and button cuffs
- Dark blue stonewash denim Levi’s 501 Original Fit jeans
- Dark brown thick leather belt with squared brass single-prong buckle
- Dark brown leather plain-toe work boots with three-eyelet derby lacing and three speed hook sets
- Black Gold Toe socks
- White cotton boxer shorts
- Omega Seamaster DeVille wristwatch with stainless 34mm case, textured black crocodile strap, and black dial with date indicator
In a pinch, this 9 Crowns lightweight flannel shirt in brown, blue, and cream flannel (via Amazon) could work, but I’d recommend searching harder to find a more vividly colored vintage piece if you want to channel Don’s look.
Do Yourself a Favor and…
I also liked “Nine Lessons from Mad Men: The Emotional Cost of Dishonesty” written by Michal Ann Strahilevitz, Ph.D., for Psychology Today, which cites examples from across the series but particularly these powerful scenes from the finale.
People just come and go… and no one says goodbye?