Jon Hamm as Don Draper, Madison Avenue ad man
Anaheim, California, October 1965
Series: Mad Men
Episode: “Tomorrowland” (Episode 4.13)
Air Date: October 17, 2010
Director: Matthew Weiner
Creator: Matthew Weiner
Costume Designer: Janie Bryant
WARNING! Spoilers ahead!
Sixty-six years ago today, Walt Disney introduced the world to “the happiest place on Earth” during a televised press event on July 17, 1955. Disneyland Park opened just one year and a day after construction began in Anaheim, California, and the sprawling theme park remains the only one completed under Disney’s direct supervision.
“Tomorrow can be a wonderful age,” Disney began when unveiling Tomorrowland, one of the nine themed “lands” that Disneyland is comprised of. “The Tomorrowland attractions have been designed to give you an opportunity to participate in adventures that are a living blueprint of our future.”
While we never actually get to see the Draper family visiting the park during their vacation in Mad Men‘s fourth-season finale, the episode’s title that we’re seeing Don forming the living blueprint for his own future, most significantly by rejecting the smart and nurturing Dr. Faye Miller (Cara Buono) to propose marriage to his bright-eyed young secretary Megan (Jessica Paré). After all, this is the man who prides himself on the fact that his life only moves in one direction: forward.
Despite this ethos, the episode presents many opportunities for Don to revisit his past. As Matt Zoller Seitz wrote for his expert entry included in the definitive volume Mad Men Carousel:
Between Don’s return to the Los Angeles bungalow of Anna Draper—the show’s most idealized recurring character—his vacation with his kids, and his starry-eyed but relentless pursuit of Megan, “Tomorrowland” sometimes feels like an hour-long psychodrama based on Don’s pitch for the Carousel in “The Wheel” (S1E13). He’s responding to nostalgia, the pain from an old wound—and trying to make the pain stop. But he can’t take Faye’s advice and do that by facing up to his past; he’s too averse to that kind of confrontation. Instead, Don tells his kids that Dick is “my nickname sometimes.” He starts to tell Megan that her engagement ring has been “in my family,” then back-pedals and describes the ring as belonging to “someone very important to me,” meaning Anna—pitiful half-truths that, coming from Don, seem like great strides toward righteousness.
Luckily for Don, who was rightly if stingingly chastised by Faye for “only [liking] the beginnings of things”, there is always California to welcome the start of his next first act. Sunny California offers as opposite a setting as possible from the dusty, dirt-poor Depression-era rural Pennsylvania where Dick Whitman got his start, so any refresh in the land of milk and honey can only set the erstwhile Dick on a happier path during his relentless drive forward.
What’d He Wear?
Far from the Manhattan office that requires Don Draper to wear the sleek gray suits that costume designer Janie Bryant designed as his “armor”, California provides Don—or Dick—with a sartorial playground that allows him to play more freely with patterns, colors, and more casual pieces befitting the warmer climate and laidback culture of the Golden State’s southern coast.
The first see of the Drapers in southern California during “Tomorrowland”, Don still looks neat in his jacket and tie, though it’s nothing like the suits we’ve seen him wear in the conference rooms at Sterling Cooper Draper Pryce. Instead, his top layer is a single-breasted sports coat made from a gray-on-stone gingham check cotton.
Gingham cotton has been a popular summer cloth for centuries, characteristic for its balanced pattern of small even checks that lack the signature twill of shepherd’s check. Due to its summery associations, gingham can often be seen in lighter colors like blue and pink—exemplified by the sporty camp shirts Sean Connery’s James Bond wears in the Bahamas during the events of Thunderball—but our “man in the gray flannel suit” stays true to his guard, dressing monochromatically in shades of gray enlivened only by the jaunty gingham.
The cut of Don’s single-breasted sport jacket reflects the trend toward shorter-length jackets as the 1960s progressed, more dramatically cut away at the bottom than the full-skirted fashions of ’50s menswear. The narrow notch lapels roll to three mother-of-pearl sew-through buttons, the three-button configuration well-balanced on Jon Hamm’s athletic 6’1″ frame. Not as shapeless as some traditional American sports coats, Don’s jacket has been tailored with wider, gently padded shoulders and a touch of waist suppression that flatters his physique.
The jacket has flapped hip pockets that are positioned with a slight backward slant, and Don frequently stashes his sunglasses in the welted breast pocket, which he wears sans the white pocket square that was another mainstay of his tailored office attire. Double vents align with the bottom of the seams running down from the back of each armpit, and each sleeve is finished with a single button at the cuff.
Don’s shirt provides more subtle sartorial evidence of his loosening up for the West Coast. While his clean white shirt and straight striped tie may suggest his office wardrobe, a closer look shows that this particular shirt is rigged with simple barrel cuffs that each close with a button, a less fussy alternative to the French-cuffed shirts that he wears exclusively to the office. Constructed of white cotton poplin, the shirt otherwise resembles many of his business shirts with its point collar, front placket, and the breast pocket for his famous Lucky Strike cigarettes.
The skinny tie reflects the monochromatism of Don’s jacket, divided into extra-wide “downhill”-direction stripes—each several inches wide—alternating in color between gray and charcoal.
Don wears dark brown trousers that harmonize with the warm stone-shaded ground of his jacket, adding a grounded but not flamboyant touch of color to his otherwise monochromatic grayscale outfit. These flat front trousers have straight on-seam side pockets, jetted back pockets, and turn-ups (cuffs) on the bottom, and they’re almost certainly held up with one of Don’s usual dark leather belts with the enclosed silver-toned buckle.
By mid-century, Americans had been particularly quick to embrace more casual slip-on shoes as appropriate footwear with suits and sport jackets. Though Don still prefers his lace-ups at the office, his stylishly dressed-down approach to dressing for California means he wears a pair of burgundy leather apron-toe tassel loafers, also worn with brown socks.
The California sun calls for both Don’s straw hat and sunglasses, the latter being his favorite American Optical FG-58 model with the squared gold frames and straight “bayonet” temples designed to flex around the head while wearing a flight helmet.
Although it’s technically fall, Don also brings his favorite summer hat, a gray-slate short-brimmed trilby made from Milanese Pinzano straw. The hat’s black band is encircled by thin mauve and gray stripes.
With the duties of his business trip behind him several days later, he wears the jacket considerably more casually over an untucked polo shirt and lighter trousers as he joins Megan and the kids for breakfast. It’s this moment where observing her kindness and patience toward them—as well as the fact that he can yield parental duties to with her—convinces him that their hotel tryst was more than just sex as his brain begins plotting just what to do with Anna Draper’s engagement ring burning a hole in his pocket.
Don wears a dark navy knitted three-button polo shirt, likely short-sleeved as we don’t see long sleeves under the cuffs of his jacket. The untucked shirt hem covers the waistband of his taupe flat front trousers, which are almost certainly held up with a belt as well and are otherwise detailed with side pockets and plain-hemmed bottoms.
“Tomorrowland” was the final episode to feature Don Draper’s Rolex Explorer I, the timepiece he had been wearing since the start of the fourth season after understandably abandoning the Jaeger-LeCoultre Reverso that his ex-wife Betty had lovingly engraved for him during their marriage. Don’s Explorer has a 36mm stainless case with a round black dial, worn on a steel Oyster-style link bracelet.
Introduced for Sir Edmund Hillary’s Mount Everest expedition in 1953, the ruggedly built Rolex Explorer was considered a “tool watch” rather than the luxurious JLC watches he had cycled through during the first few seasons and the Omega DeVille he would wear from the fifth season through the end of the series.
How to Get the Look
Don Draper’s worlds collide when he brings his children on a business trip to the land of sunny new beginnings in southern California, blending his personal and professional lives as well as his past and his future. He loosens his office-wear armor as he strides through “Tomorrowland” in a cool-wearing gingham check cotton sports coat, worn casually with a navy knit polo and more dressed up with a white shirt, skinny tie, and sun-shielding straw trilby.
- Gray-on-stone gingham check cotton single-breasted 3-button sport jacket with narrow notch lapels, welted breast pocket, slightly slanted flapped hip pockets, 1-button cuffs, and double vents
- White cotton shirt with point collar, front placket, breast pocket, and button cuffs
- Gray-and-charcoal extra-wide “downhill”-striped skinny tie
- Dark brown flat front trousers with belt loops, straight/on-seam side pockets, jetted back pockets, and turn-ups/cuffs
- Burgundy leather apron-toe tassel loafers
- Dark brown socks
- Gray-slate Pinzano straw short-brimmed trilby with a colorful-striped black band
- American Optical Flight Goggle 58 (FG-58) square-framed aviator sunglasses in yellow gold with brown lenses and “bayonet” temples
- Rolex Explorer I with a stainless 36mm case, black dial, and stainless Oyster-styler link bracelet
Do Yourself a Favor and…
Check out the fourth season.