Jon Hamm as Don Draper, former ad man in search of himself
Oklahoma to California, Fall 1970
Series: Mad Men
– “The Milk and Honey Route” (Episode 7.13), dir. Matthew Weiner, aired 5/10/2015
– “Person to Person” (Episode 7.14), dir. Matthew Weiner, aired 5/17/2015
Creator: Matthew Weiner
Costume Designer: Janie Bryant
WARNING! Spoilers ahead!
To honor the anniversary of Jack Kerouac’s On the Road, published today in 1957, I’m taking a look at “The Milk and Honey Route,” the penultimate episode of Mad Men in which Don Draper’s journey to find himself drives him through the heart-land of darkness.
I’ve always romanticized the idea of the Great American Road Trip, a nostalgic journey through the land of “googie” architecture, of lonely motels and diners now mostly dormant along the old U.S. Route 66. As a result, I’ve always been drawn to “road movies” like Planes, Trains, and Automobiles, Carol, and Rain Man that find its characters forced to forego the more “efficient” travel method of flying, instead traveling by car through the core of America’s heartland. Needless to say, I was thrilled when Don Draper’s seven-season narrative on Mad Men seemed to be wrapping up with his motor trip through the titular “milk and honey route” of the series’ penultimate episode.
Don’s journey across the continent in these final episodes markedly contrasts to the slick “jet set” vibes of his previous trips out to his beloved California that are well chronicled in the show’s earlier seasons and even in the premiere of the first part of the seventh season. Don’s coast-to-coast air trips have always provided him the luxury of skipping the opportunity of finding himself in favor of processed air travel. Now, behind the wheel of his five-year-old Cadillac, it’s just him and the chance to find out more about himself and his country.
When Don’s Cadillac encounters some car trouble, the former ad man gets a look behind the curtain of this oft-romanticized nostalgia of small-town America, a place that advertises itself as warm and welcoming… until it isn’t.
Take Del (Chris Ellis) and Sharon Hill (Meagen Fay), the proprietors of the Sharon Motel in rural Oklahoma. Don is dropped off at the motel where Del and Sharon are quick to accept him as one of their own, appreciating his handiness, inviting him for roast dinners, and even including him in one of Del’s American Legion get-togethers. It’s this latter inclusion that gives Don the greatest anxiety; after all, Dick Whitman has spent the better part of two decades forever anticipating the moment he’s been called to account for his desertion in Korea that began with the death of his commanding officer. However, Don is able to find some semblance of kinship with these strangers who understand the tolls of war, not just on humanity but on the individual.
Unfortunately, a few shared bars of “Over There” aren’t enough to build unwavering trust. We see how quickly the town is to turn on Don, whose demographic defines him as presumably of their own kind, and we can only imagine how they would treat an outsider.
The theft of funds from the Legion hall turns all eyes against the shifty outsider with his fancy car and bulging money clip. As a bourbon-soaked Don sleeps off his hangover, Sharon meekly unlocks the door to his motel room and Don awakes to find himself surrounded by Del and his drunken comrades-in-arms, who are quick to accuse and even quicker to take the keys to Don’s “probably stolen” car as collateral until the money is returned. That particular accusation must strike a particular chord with Don, whose entire life – and the cars, clothes, and cash that it afforded – have all been stolen by his appropriation of Lieutenant Donald Draper’s identity in 1950.
In a way, Don’s accusers weren’t wrong to target him, as it was Andy (Carter Jenkins), the motel’s young “maid” and fledgling hustler in whom Don sees the worst of his young self, that was responsible for the theft. “I’m not paying for the room,” Don declares to the scowling Del as he hands over the money and leaves with Andy in tow. A few miles outside of town, Don pulls over at a bus stop. He hesitates a second, then tosses the keys to his Cadillac in Andy’s lap. “Pink slip’s in the glove box,” Don tells him. “Don’t waste this.”
And thus… Don persists. “The final shot shows Don alone on the roadside with nothing but cash and a bag of clothes,” wrote John Teti for The AV Club. “He smiles with relief. His disappearing act is nearly complete. All that remains to vanish is himself. Then they’ll never catch up to him.”
What’d He Wear?
(Note: This analysis does not include the denim workwear that Don also wears frequently in the finale episode, “Person to Person”, as that particular aesthetic will receive its own BAMF Style post.)
The Mint Green Polo Shirt
“The Milk and Honey Route” (Episode 7.13) begins with Don Draper calling his daughter Sally from a motel room in Kansas, describing his “milk and honey route” road trip to her. It’s late September 1970, and it’s been a few weeks since he abandoned his enviable position at the advertising super-agency of McCann-Erickson in New York.
Though he’s dressed down, Don’s casual aesthetic initially looks similar to his weekend attire during his days in advertising. He kicks back in the motel room with a mint green double-knit polyester polo shirt with short sleeves and a breast pocket for Don to keep his Old Gold cigarettes (lest we forget, he stopped smoking Lucky Strikes after they dropped his agency!) There is white piping on the shirt’s large collar and on each side of the four-button placket that extends down to mid-chest.
The same shirt makes another appearance a week later when Don wears it with his blue bomber jacket and khaki trousers as he returns to the Sharon Motel. His Cadillac fixed, Don allows the motel owner Del to talk him into joining Del’s fellow Legionnaires for an evening of drinking and stories. A desperate Del also offers Don two free nights at the motel if he fixes the Coke machine. How interesting… just as Don had appealed to McCann-Erickson for his ability to service the Coca-Cola account, even here he can’t evade people wanting him to service Coke.
The mint green polo shirt makes a final appearance during the first day of activities at the Big Sur retreat in “Person to Person” (Episode 7.14), when he wears it with a pair of light tan chinos, brown leather loafers, and black socks.
A white-stitched umbrella logo on the top of the breast pocket indicated to me that this was likely a vintage piece, so I did some digging and found a nearly identical shirt in black at the online vintage retailer Rusty Zipper that identified it as a polyester shirt offered by the Arnold Palmer brand in the 1970s.
“What about an umbrella?” Arnie had reportedly asked his corporate team when establishing the brand in 1961. Read more about the history of the Arnold Palmer brand here.
Blue-and-Cream Plaid Shirt
The day after his phone call with Sally, Don is driving through rural Oklahoma when his Cadillac runs into some mechanical trouble. He gets a ride from the tow service – based out of Alva, Oklahoma – to the local Sharon Motel, where he meets the proprietors Del Hill (Chris Ellis) and his wife Sharon Hill (Meagen Fay), for whom Del’s hotel is named. Don’s only luggage is a rumpled bag from Sears, indicating that all of the duds we’re seeing on screen are likely from that venerated American department store. (In fact, you can still find an almost identical shirt by St. John’s Bay available from J.C. Penney.)
The summery plaid shirt Don is wearing is almost assuredly from his new Sears collection, a non-threatening short-sleeved cotton shirt with a large button-down collar, front placket with mother-of-pearl buttons, and breast pocket for his cigarettes. It’s slightly oversized for Don’s fit physique, showing us that the ad man’s “made-to-measure” days are behind him and looking more like something from your dad’s closet.
The shirt pattern consists of blue double stripes criss-crossing against a cream ground, with both sets of stripes bisected by a slim tan stripe. The shirt has a long curved hem, as it is meant to be worn tucked in. When Don first arrives at the motel, he does indeed have it tucked in to his dark brown trousers.
This shirt makes another appearance a few nights later when the TV in Don’s motel room goes out (and in the middle of a Redd Foxx joke, no less!), sending him to the motel’s lobby to inform Sharon as The Platters’ sleepy “Harbor Lights” plays. After Don fixes her old Royal typewriter and volunteers that he was in “the service”, she pays off the favor by inviting Don on her husband’s behalf to an upcoming military reunion: “everybody who’s a vet and likes drinking will be at the Legion on Saturday night”.
Green-and-Orange Plaid Shirt
Don’s other plaid shirt worn during his stay at the Sharon Motel in “The Milk and Honey Route” (Episode 7.13) is a more complex plaid pattern in autumnal shades of orange and hunter green mixed with black and translucent white. It buttons up the plain front (no placket) with six mother-of-pearl buttons and a small loop that extends from the left side of the collar for a seventh button at the top.
The short-sleeved shirt is styled more like a classic sport shirt with its camp collar and trim fit with a short hem meant to be worn untucked. Of course, Don still needs a place for his smokes, so the shirt has a pocket over the left breast.
The shirt makes its first appearance as Don reads Mario Puzo’s The Godfather in his room at the Sharon Motel in rural Oklahoma, kicking back in khakis and no socks. Finding out that the car part his wounded Cadillac needs has to come from Tulsa, he tells the motel “maid”, Andy, that: “I’m gonna need another book.”
Don wears the shirt again when he leaves the motel about a week later, having been blamed for Andy’s theft of the funds raised during the Legion dinner. In addition to a serious grimace, he wears his blue bomber jacket and brown slacks as he tosses the money back to Del.
Don’s autumnal-plaid sport shirt shows up again in “Person to Person” (Episode 7.14) when he calls Sally from Utah, having just witnessed Gary Gabelich’s Blue Flame breaking the land speed record at Bonneville Speedway on October 23, 1970. Sally, in turn, breaks the news about Betty’s lung cancer diagnosis. Don reacts as one would expect him to, but Sally is the true hero of this tough call. “I’m not being dramatic. Now, please, take me seriously,” she urges as she offers thoughtful suggestions on what he should do.
This shirt makes its final appearance for a sunset walk at Big Sur, when Don wears it with a pair of jeans.
Blue Bomber Jacket
Don’s outerwear for this leg of his journey is primarily a blue nylon jacket, which a helpful Instagram commenter (@relicvintage) identified as a product by Derby of San Francisco, an iconic brand that had been producing this jacket since the early 1960s. Vintage examples can be found online (see here), but the style was revived in 2012 by Iraq War veteran Victor Suarez. “It was the workingman’s jacket,” Suarez told the San Francisco Chronicle. “Once you wear a Derby, your whole attitude changes.”
The style appears to be inspired by the classic MA-1 bomber jacket with its zip front and dark knit collar, cuffs, and hem. The jacket has a yoke that extends across the chest and shoulders, and there are two slash-style hand pockets. There is also a button at the top of the jacket and two on the waistband.
The zipper begins a few inches above the waistband. Unlike a classic bomber jacket, the elasticized hem only extends around the back rather than the full waist.
Don wears this Derby jacket with all three of his “road” shirts while at the motel and with both pairs of trousers. Per Tom and Lorenzo in their fantastic blog exploring the style of Mad Men, Don’s jacket “is pretty much an exact match to the blue Betty’s wearing in the previous scene, where she gets news that is going to affect Don’s life on a profound level,” signifying a subconscious familial tie.
Gray Suit Jacket
The only other coat that Don wears during this leg of his road trip is the gray self-striped jacket from the business suit he was wearing when he left New York in “Lost Horizon” (Episode 7.12). This suit was arguably the trendiest of those worn by Don during the seventh season with its wide notch lapels and long single vent on the single-breasted, two-button jacket. The jacket also has a welted breast pocket, though Don foregoes a pocket square, and wide flapped hip pockets with swelled edges like the lapels.
You can read more about this whole suit in my post from July 2018. The suit jacket makes its appearance when Don attends the American Legion fundraiser in “The Milk and Honey Route” (Episode 7.13) orphaned with a pair of khaki chinos rather than the suit’s matching trousers. Once again, I refer you to the excellent prose of Tom and Lorenzo as they explore the subtext of Don’s clothing – and how he wears it – in this scene:
Note that Don puts on a little bit of his old Don Draper armor – that suit jacket and white shirt – to enter a situation that felt slightly threatening. Note also that this is the suit Don was wearing when he walked out of McCann and out of his old life. More importantly, he walked out of a meeting in which a slick marketing research guy was describing a mythical middle-American male full of likable attributes and benign good will. Nothing like the violent, ignorant, xenophobic men Don encountered in the real middle-America; the one not mythologized by Madison Avenue. There’s a reason the radio was playing “Okie from Muskogee” in Don’s dream. It’s because the lyrics were all about that tension between coastal and middle America; a tension which grew during the cultural revolution and which has informed all of American politics in the half-century since. Don looks like exactly what he is here: a city slicker slumming with the locals. And despite their faux and forced good will toward him in this scene, it became obvious that the locals saw him in exactly that way.
Don wears one of his classic dress shirts, though he wears it without a tie and the contrast of the shirt with the white undershirt visible under his open neck reveals it to be more of an eggshell color. The shirt has a semi-spread collar, front placket, breast pocket, and double (French) cuffs that are fastened with a set of steel rectangular links with black onyx rectangular settings.
In a nod to continuity, these appear to be the same cuff links that he was wearing with the suit and shirt when he left New York.
Brown and Khaki Trousers
All of Don Draper’s trousers, aside from his jeans, in the last two episodes are varying shades of brown, indicative of his abandonment of the grays and navy blues of the business world as he embraces the earthiness of his new adventure. In total, he appears to cycle through three pairs of trousers during his drive from Oklahoma to California, all flat-fronted straight-leg trousers with belt loops, side pockets, jetted back pockets, and plain-hemmed bottoms.
Don’s “driving” trousers in “The Milk and Honey Route” (Episode 7.13) are a pair of dark tobacco brown slacks, worn with a black belt that closes with a gold single-prong buckle. He wears these for his arrival at and his departure from the Sharon Motel.
When Don is temporarily grounded due to car trouble in Oklahoma, he lounges about in his room and attends the local American Legion in a pair of warm khaki slacks, also worn with a black belt.
By the time Don ventures further west into Utah and, eventually, the Big Sur retreat in California, he wears a pair of lighter tan trousers in a lightweight chino cloth. These trousers appear to be styled slightly different from the others with no belt loops and buttons on the back pockets.
A Penney’s bag in his Utah motel room indicates that these newly seen trousers may have been a purchase from Penney’s, as the brand was known until it was re-branded as J.C. Penney in 1971.
When you’re living out of a shopping bag, you hardly need the extra weight of additional shoes. That said, you’ll be making the most of one pair of shoes, and they should be both durable and versatile. Don thus engages on his cross-country adventure with just a pair of walnut brown leather moc-toe penny loafers.
Don’s brown Brooks Brothers penny loafers prove their versatility as he is able to wear them dressed up with a suit jacket and dressed down when stepping out to the motel swimming pool… and nicely suited for all casual occasions in between. He foregoes socks when he heads out to the pool, but he otherwise wears exclusively black dress socks with the distinctive gold acetate threading on the toes that modern shoppers would recognize as the Gold Toe brand.
Currently the third largest producer of American socks, Gold Toe will be celebrating its 99th anniversary this Saturday. The brand started life on September 8, 1919, at Great American Knitting Mills in Berks County, Pennsylvania. During the Great Depression in the 1930s, as men were wearing holes in their socks and unable to afford to buy more, the company reinforced the toes with high-quality Irish linen and added gold threading to make them easily distinguished for department store shoppers looking to purchase this durable hosiery. After enjoying massive success in its segment for the better part of a century, Great American officially changed its name to Gold Toe Brands, Inc., in 2002.
During the warm evenings from motel room to motel room, Don often strips down to his underwear for solitary nights with a bottle of booze and late-night TV. As seen through the entire show’s run, this never deviates from his white cotton crew-neck T-shirts and white cotton boxer shorts with elasticized waistbands.
Possibly encouraged by Andy’s report that the motel pool is now “piss”-free, Don struts out to the swimming hole in a pair of short-inseam navy swim trunks with red-and-white piping on the bottom hems and on the top and bottom of the front waistband, which closes with a single white button.
Don wears these swim trunks with his autumnal-plaid short-sleeve sport shirt, brown penny loafers, and – of course – his sunglasses.
Don Draper wore several pairs of sunglasses over the run of Mad Men, but his signature pair is arguably the American Optical Flight Goggle 58 that he wore early in the show’s run. After a brief flirtation with the space-age Ray-Ban Olympian during the sixth season, eyewear expert Preston Fassel confirmed that Don’s gold-framed aviator sunglasses in these seventh episodes are the actually Ray-Ban Caravan model, a similar shape to his original AO FG-58 shades, but differentiated as “the Caravan is given away by its thinner temples, shorter height, and more rectangular shape,” according to Mr. Fassel.
You can read more about Don’s sunglasses in Preston Fassel’s incredibly researched article for 20/20 Magazine in March 2016, where the author busts open the oft-reported falsehood that Don wears Randolph Engineering sunglasses.
Don may hand over the keys to his Cadillac Coupe de Ville, but he doesn’t show any desire to rid himself of his Omega Seamaster DeVille, a classic timepiece evoking timeless, understated luxury with its slim steel 34mm case, black cross-hair dial with 3:00 date window, and textured black leather strap.
A Christie’s auction from December 2015 sold four watches that had appeared on the show, including Don’s Omega which sold for $11,875.
According to the auction listing, “the watches were leased to the show by vintage watch specialist Derek Dier, who has supplied watches to the movie industry, noted musicians, actors, writers, artists, international dignitaries and Fortune 500 CEOs. Mad Men Property Master Ellen Freund worked with Dier to select the watches.” The Christie’s page further describes the watch as: “Signed Omega, Automatic, Seamaster, De Ville, Ref. 166.020, Movement No. 23’943’081, Circa 1960.”
What to Imbibe
Now far from the luxurious cocktail bars of New York City, we see what Don drinks when he’s got nothing to prove. Rather than taking slugs from an office bottle of Canadian Club while prepping for a pitch or smoothly ordering another Old Fashioned while a beautiful beehive-haired woman stares from across the bar, Don chooses the humble Coors Banquet beer as his brew of choice when holed up in a Kansas motel room and excitedly sharing details of his “milk and honey route” road trip in Sally.
Later in Utah, after another phone call with Sally, Don preps himself for a difficult conversation with Betty by drinking Stag beer, now a Pabst brand that currently advertises itself as “first brewed before your granddad was born.” Originally brewed in Belleville, Illinois, in 1851, this budget beer enjoys a popularity among hard drinkers for its low sugar content and among hipsters for its vintage aesthetic.
In “The Milk and Honey Route”, Don fuels his week of boredom in the Oklahoma motel room with lower-priced bourbon. Looking for something – anything – to do, Don pays Andy to “rustle up a bottle” of something to drink. Andy returns to Don with a bottle of Old Granddad, charging another $10 to hand it over. Don begrudgingly pays and offers the boy a drink, but Andy refuses: “I’m 1/8 Comanche, don’t touch it.”
At the local American Legion reunion and fundraiser, Don gets hammered on Old Crow while his new “pals” drink Lone Star beer.
What to Drive
It’s not #CarWeek, but Don’s Caddy gets so many glamour shots in its penultimate episode, that I feel behooved to give it a little more love than just a few sporadic mentions scattered throughout this post. (This same content, with different photos, appeared in an earlier post about Don’s final suit.)
Don Draper drives across country in the 1965 Cadillac Coupe de Ville that he has been driving since the fifth season premiere. This silver ’65 Coupe de Ville replaced Don’s earlier Caddy that he purchased in the show’s second season when a salesman convinced him that it was the car he needed for proving his success to the world.
1965 was the first model year of the redesigned third generation Cadillac Coupe de Ville, though it continued the 129.5-inch wheelbase of its predecessor and the 429 cubic-inch V8, though the engine would be increased in size to a 472 cubic-inch V8 for the 1968 model year. The Coupe de Ville would undergo another redesign for 1971.
1965 Cadillac Coupe de Ville
Body Style: 2-door convertible
Layout: front-engine, rear-wheel-drive (RWD)
Engine: 429 cid (7.0 L) Cadillac V8 with Carter 4-barrel carburetor
Power: 340 hp (253.5 kW; 343 PS) @ 4600 rpm
Torque: 480 lb·ft (651 N·m) @ 3000 rpm
Transmission: 3-speed automatic
Wheelbase: 129.5 inches (3289 mm)
Length: 224.0 inches (5690 mm)
Width: 79.9 inches (2029 mm)
Height: 55.6 inches (1412 mm)
In August 2015, less than three months after the show’s finale aired, the actual ’65 Cadillac Coupe de Ville driven by Don in the show was auctioned by Screenbid, yielding $48,980. As Bob Sorokanich noted for Road & Track, the “sale price includes $39,500 for the car, plus a 24 percent commission to Screenbid, the auction host. That’s pretty strong money for a ’65 Coupe de Ville, which Hagertys tends to value around $13,000.”
“De Ville” was evidently the theme of Don’s luxurious life from the fifth season onward, as that season premiere introduced both his new Cadillac Coupe de Ville and the Omega Seamaster DeVille that he would have through the end of the series.
How to Get the Look
Don Draper’s road closet puts function before fashion, comfortable enough to wear for long periods of sitting behind the wheel of a car or against the headboard of a motel bed while also respectable enough to gain the [initial] trust of the folks he meets along the way. By wearing clothes that all follow the same general color scheme, Don is more able to mix and match for a relatively wide variety of outfits from his limited selection.
- Mint green double-knit polyester short-sleeve polo shirt with white-piped collar, four-button placket, and breast pocket
- Blue-on-cream plaid cotton short-sleeve shirt with large button-down collar, front placket, breast pocket, and curved hem
- Green, orange, black, and white plaid short-sleeve sport shirt with camp collar, plain front, breast pocket, and straight hem
- Blue nylon bomber-style zip-front Derby of San Francisco jacket with dark blue knit collar, cuffs, and waistband
- Dark brown flat front trousers with belt loops, side pockets, jetted back pockets, and plain-hemmed bottoms
- Khaki flat front trousers with belt loops, side pockets, jetted back pockets, and plain-hemmed bottoms
- Light tan chino-cloth flat front trousers with belt loops, side pockets, jetted button-through back pockets, and plain-hemmed bottoms
- Navy short-inseam swim trunks with red-and-white piping
- Walnut brown leather moc-toe penny loafers
- Black dress socks with gold toes
- White cotton crew-neck T-shirt
- White cotton boxer shorts
- Black leather belt with gold-toned single-prong buckle
- Omega Seamaster DeVille wristwatch with stainless 34mm case, textured black crocodile strap, and black dial with date indicator
- Ray-Ban Caravan gold-framed aviator sunglasses
For a road trip across the Midwest in summer 2019, your humble blogger took a page from Don Draper’s style book and dressed in a vintage brown plaid short-sleeved sport shirt from Mervyn’s over a white crew-neck undershirt with brown flat front Lee trousers, brown Dockers penny loafers, and my usual prescription Ray-Ban aviator sunglasses. Though not necessarily Don-inspired, I wore my new gold-and-steel Invicta Speedway watch (Invicta’s tribute to the Rolex Daytona) in the spirit of the long drive. The July weather was a bit too hot for my blue nylon zip-up jacket, but it would have provided lightweight protection against the rain, should I have encountered any. To see my tribute look in action at an Ohio Turnpike rest stop, click here.
Do Yourself a Favor and…
You weren’t raised with Jesus. You don’t know what happens to people when they believe in things.
Tidbits on the title from John Teti’s review for The AV Club:
The episode’s title comes from a bit of early 20th-century hobo lingo: A “milk and honey route” was a train route that offered plenty of food for a scavenging wanderer of the American countryside. In a 1930 book that was also named for the term… author Nels Anderson writes, “Any railroad running through a valley of plenty may be called a milk and honey line. But this is a transient term; what may be a milk and honey route to one hobo may not be so to another.” Indeed, the route rejected by Don ends up bestowing a rich bounty on Pete.
Both Don and Pete mention Kansas, although Don leaves just before Pete is about to start a new life there. He always ends up following Don one way or another.