Don Draper’s Teal-and-Turquoise Shirt in “Tomorrowland”

Jon Hamm as Don Draper on Mad Men (Episode 4.13: "Tomorrowland")

Jon Hamm as Don Draper on Mad Men (Episode 4.13: “Tomorrowland”)


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!


During my latest Mad Men rewatch while on lockdown due to the coronavirus pandemic, I found myself so intrigued by the fourth season finale that I watched the episode back-to-back. For a show set so far into the past, it’s amazing how effective Mad Men can be at stirring a viewer’s enthusiasm for the future.

When this episode first aired in October 2010, I was beginning my senior year of college, as unsure about what my future would look like as it I was when I had first moved into my crowded dorm room three years earlier. I had no clear picture of what my “Tomorrowland” would look like, whether I’d manage to land a fulfilling job, a healthy romantic life, or even whether the ever-present specter of dark suicidal urges would cut both of those prospects from being fulfilled. I’d been watching a season of Don Draper weaving from rock-bottom lows to promising highs, and the once self-destructive ad man’s future looked brighter than ever as he ended the season with all signs pointing to a favorable future.

This trajectory began during a business trip-turned-family vacation to Disneyland, for which Don brings along his secretary Megan (Jessica Paré), who has already developed a respectful relationship with the Draper children… and a casually carnal relationship with their father. Megan’s presence with the family seems strictly professional, serving in the role of babysitter after Don’s ex-wife Betty (January Jones) had impulsively fired the children’s long-time nanny Carla (Deborah Lacey) and left Don in desperate need for someone to watch the kids while he conducts business.

The episode even seems to tease chemistry between Don and Megan’s college “frenemy” Camille, a blonde in the tradition of former Draper paramours Betty, Bethany Van Nuys, and even Dr. Faye Miller (on a purely aesthetic basis), but the show averts our expectations that Don would continue his pursuit of meaningless sex by revealing that it’s Megan he visits later that Saturday night, following his heart… not to say that other organs may not have still had a say.

Matthew Weiner was never casual with his episode titles and, while “Tomorrowland” carries the obvious associations with the futuristic section of Disneyland that will no doubt be on the Draper family’s agenda, it suggests Don designing the architecture of his own Tomorrowland. After nearly two years of depressive drinking and drifting, he’s finally found what could be the key to his elusive happiness… and, of course, he found it in California, the seaside state that has long represented his fondness for fresh beginnings.

What’d He Wear?

After rewatching the series earlier this year, I knew I would want to feature one of Don Draper’s dressed-down looks from “Tomorrowland” for a summertime #MadMenMonday post, so I posted an Instagram poll: should I write about this blue duotone shirt or his gun club check sport jacket and tie? More than half of the nearly 600 respondents voted for this shirt (and I thank you for choosing the less complicated outfit to describe!)

At first, I assumed this was the plaid sports shirt we had seen Don wearing during the solar eclipse in “Seven Twenty Three” (Episode 3.07) and again while journaling in “The Summer Man” (Episode 4.08), but the “Tomorrowland” notably lacks the high-contrasting brown checks.

This shirt is patterned in a large-scaled mottled blue two-tone check, alternating between a low-contrast teal and turquoise with a yellow windowpane grid separating these colors from each other. The short-sleeved shirt has a sporty collar that serves as a unique blend of a traditional camp collar and the elegantly rounded roll of a “Lido collar”. The shirt fastens with five flat clear plastic two-hole buttons up the front, with the top button located about two inches down from the neck; Don wears the button open, likely by design as the shirt may look awkward when fully buttoned. Don’s shirt is also detailed with a set-in pocket over the left breast.


An Army man, Don would be comfortable in the durable chino cloth trousers now colloqualized as “khakis”, so he continues lounging in his hotel room in a pair of beige chino cotton flat front trousers which he has self-cuffed at the bottoms. Though the trousers have belt loops, Don understandably foregoes a belt.

Le Carré and High Life for a lonely night in the hotel. Note the apparent continuity error where Don isn't wearing his Rolex, though it would appear on his left wrist in the subsequent shot.

Le Carré and High Life for a lonely night in the hotel. Note the apparent continuity error where Don isn’t wearing his Rolex, though it would appear on his left wrist in the subsequent shot.

In addition to the pockets along the side seams, these trousers have jetted back pockets, and he folds the Disneyland brochure into the back right pocket to support his weak excuse of visiting Megan’s room to go over their plan for visiting the park the following day. (“Do you think I should be involved in such high-level decisions?” she sarcastically responds.)

Don puts on a pair of dark cordovan leather tassel loafers, ostensibly worn without socks, when he visits Megan’s room.

Megan brings Don out onto her balcony to "enjoy the view".

Megan brings Don out onto her balcony to “enjoy the view”.

After two years of wearing a gold Jaeger-LeCoultre Reverso dress watch that had been personalized with an inscription from his now ex-wife, Don understandably abandoned that watch sometime after his separation from Betty and began wearing a Rolex Explorer, perhaps signaling that the newly single Don Draper would spend much of the fourth season exploring himself (I know it’s a stretch, but let me have this one!) The choice to rig Don with a Rolex also aligns him with James Bond, who would have been a major cultural icon by Mad Men‘s fourth season as Sean Connery had already played the globe-trotting 007 in three films, wearing a Rolex Submariner on his wrist for all three. (Bond’s literary creator, Ian Fleming, actually preferred a Rolex Explorer.)

Don wears a stainless steel Rolex Explorer I with the classic 36mm case that had been standard for much of the watch’s run since it was first introduced for Sir Edmund Hillary’s Mount Everest expedition in 1953. Worn on a steel Oyster-style link bracelet, the watch has a black dial with a luminous reverse triangle at 12 o’clock and the reference’s characteristic 3-6-9 Arabic numerals.

Don plans out a day at Disneyland with his kids Sally (Kiernan Shipka), Bobby (Jared Gilmore), and Gene, though an isolated night in a hotel room may be closer to the reality for many family vacations in 2020.

Don plans out a day at Disneyland with his kids Sally (Kiernan Shipka), Bobby (Jared Gilmore), and Gene, though an isolated night in a hotel room may be closer to the reality for many family vacations in 2020.

Rolex Explorer, ref. 1016, circa 1969 (Source: Hodinkee)

Rolex Explorer, ref. 1016, circa 1969 (Source: Hodinkee)

Some have argued that, while not impossible that Don Draper would have had this watch in 1965, it would have been highly unlikely for the typical American businessman—especially a more conservative “man in the gray flannel suit” type—to wear this kind of sports watch every day with everything from suits to sport shirts. (And, indeed, some have argued that it’s a more recent model that would be anachronistic anyway.)

In my mind, I’ve formed two possibilities:

  1. Don, an avid reader, noticed Ian Fleming’s description of Bond’s “heavy Rolex Oyster Perpetual on an expanding metal bracelet” in On Her Majesty’s Secret Service and decided that he had found the watch he needed for the next phase of his life.
  2. During the early months of his newly single life in 1964, Don’s romantic entanglement with an international stewardess found him in Switzerland where the latest Explorer caught his eye from the Rolex boutique window.

Should the latter have been the case, it would make sense that he would abandon the watch when settling into his new life with a new woman for the seasons to follow.

What to Imbibe

Don Draper may be famous for reviving the Old Fashioned in pop culture (unless you’re one of those Wisconsinites who has been enjoying brandy and Sprite this whole time), but the erstwhile Dick Whitman almost just as frequently drank beer, whether fueling himself while building a playhouse for his daughter, journaling his summer of rejuvenation, or washing down an intriguing John le Carré paperback while trying not to think about the intriguing French-Canadian beauty in the adjacent room.

For moments like the latter, Don turns to the preeminent “champagne of beers”, Miller High Life.

Champagne of beers or not, Don realizes he's more than willing to let his newly purchased sixer go untouched if Megan has already returned from Whisky a Go Go.

Champagne of beers or not, Don realizes he’s more than willing to let his newly purchased sixer go untouched if Megan has already returned from Whisky a Go Go.

High Life has remained the flagship of the Milwaukee-based Miller Brewing Company since its conception in 1903. The high levels of carbonation in this 4.6% ABV pilsner created an abundance of bubbles that led to its original appellation of “the Champagne of Bottle Beers” before taking its catchier, shortened modern form.

Though Don is seen drinking all of the “big three” flagship American brews across Mad Men‘s seven-season run, it’s Miller High Life in both bottle and can form that he enjoys with the greatest frequency, beginning with “Flight 1” (Episode 2.02) and ending with this lonely night in the

Jon Hamm as Don Draper on Mad Men (Episode 4.13: "Tomorrowland")

Jon Hamm as Don Draper on Mad Men (Episode 4.13: “Tomorrowland”)

How to Get the Look

“Tomorrowland” illustrates a comfortable and accessible way to emulate Don Draper’s timeless style without needing to keep your cuff links in place as his casual muted plaid sport shirt and ageless khakis suit him just as well for a night with family, lounging in solitude, or a romantic rendezvous.

  • Teal-and-turquoise large-scale check (with yellow windowpane grid) short-sleeved sport shirt with Lido/camp hybrid collar, plain front, and set-in breast pocket
  • Beige chino cotton flat front trousers with belt loops, zip fly, straight/on-seam side pockets, jetted back pockets, and self-cuffed bottoms
  • Dark cordovan leather tassel loafers
  • Rolex Explorer I with a stainless 36mm case, black dial, and stainless Oyster-styler link bracelet

While short-sleeved men’s shirts, specifically camp shirts, seem to be abundant from major retailers in summer 2020, your best bet for a shirt like this would still be to explore vintage outfitters like Rusty Zipper, where this Draper-style sport shirt is currently offered for $40.

Do Yourself a Favor and…

Check out the fourth season.

The Quote

I want to know if I can knock on this door again tomorrow night or if this is just what it is.


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