Don Draper Smokes Hashish in a Cream Silk Sportcoat

Jon Hamm as Don Draper in

Jon Hamm as Don Draper in “A Tale of Two Cities”, Episode 6.10 of Mad Men.


Jon Hamm as Don Draper, Madison Avenue ad man

Los Angeles, August 1968

Series: Mad Men
Episode: “A Tale of Two Cities” (Episode 6.10)
Air Date: June 2, 2013
Director: John Slattery (yes, Roger Sterling)
Costume Designer: Janie Bryant


I thought it was appropriate to commemorate the smokers’ holiday of 420 by checking out Don’s first experience with hashish. This isn’t the first time we’ve seen Don enjoying the happy plant (remember Midge’s friends in the first season?), but it’s certainly significant for him.

“A Tale of Two Cities” finds Don and Roger with Harry in L.A. The title may lead some to assume that the “two cities” are naturally L.A. and New York, but I believe the second city is Chicago (rather than New York) due to the 1968 Democratic National Convention providing the episode’s backdrop. While police are taking on protestors in the Windy City, Don and company head to a hip Hollywood party… arriving in style in Harry’s beautiful (but unappreciated) red Mustang convertible.

What’d He Wear?

In July 2015, began auctioning many items featured on the show, including this whole outfit, which is described as: “a linen sports coat, a white long-sleeve button-up dress shirt, Angelico-made gray pants (with “Don” written inside), a silk tie with brown and turqoise [sic] vertical stripes, and silver-colored cufflinks with four triangles.” The sport coat is a size 42, and his shirt has a 16.5 neck and a 35 sleeve.

Don's whole outfit from this sequence, as auctioned by Note how much more wrinkled the linen looks here.

Don’s whole outfit from this sequence, as auctioned by Note how much more wrinkled the linen looks here.

Don’s raw silk sport coat and slacks is a much more timeless look than Roger’s hip swinger attire, but it’s still firmly rooted in the fashion of his early ’60s heyday. However, both Don and Roger arguably look better than Harry with his “man-of-the-moment” LA hipster get-up that would become sadly dated in months. You can tell so much about each man just by seeing how they dress for a party.

How to look stylish, fashionable, and trendy - respectively - in 1968. Despite what some may say, these three words are not synonyms.

How to look stylish, fashionable, and trendy—respectively—in 1968. Despite what some may say, these three words are not synonyms.

BAMF Style commenter “Badwolf” kindly—and awesomely!—pointed me in the direction of an AMC clip featuring the talented Janie Bryant talking about Don’s, Roger’s, and Harry’s outfits in this episode.

After discussing Roger’s “yachting” look, Bryant pulls out Don’s sport jacket, marveling over the tan tonal-striped silk lining and the material itself:

This is the sports coat that I designed for Don, and actually I thought I was going to use it for the premiere episode, but I ended up using brighter colors for the premiere episode, and I was just waiting for the perfect moment for Don to be in this beautiful ivory raw silk sports coat…

Raw silk? But-but-but I thought it was linen… I’m ashamed to say I was relatively unfamiliar with raw silk before seeing this video. After doing some more research, I discovered—to my credit—that raw silk looks more like a slubbed linen than silk. In fact, I even discovered a vintage 1960s jacket made from the same ivory cream-colored raw silk as the one seen on the show! Silk would probably be the more luxurious Draper option, but I would likely still sport linen for its cool-wearing properties.

It’s very minimal in color, it has this elegance to it. It’s very masculine; it’s all the things I think of when I think of Don Draper.

Don always wisely dresses for his environment, so shifting from New York City to a warm summer party in Los Angeles makes his cream-colored raw silk sport jacket a respectable choice.

This sort of activity would cause more of a wrinkle in his pants than his jacket anyway.

This sort of activity would cause more of a wrinkle in his pants than his jacket anyway.

Don’s sports coat is single-breasted with a two-button front and edge-stitched notch lapels. The shoulders are slightly padded with roped sleeveheads and three buttons on each cuff made from the same light brown horn as the front buttons. The jacket has three outer patch pockets: one on the left breast and one on each hip. The sport jacket has double vents that are a reasonable length, bridging the super short vents of the earlier decade and the longer 12″ vents that would become popular in the ’70s.

Don can't help but to look awesome in any setting, regardless of his comfort level.

Don can’t help but to look awesome in any setting, regardless of his comfort level.

Since it’s a party, Don lets himself go crazy by not wearing a white shirt for once… instead, it’s a pale ecru. Otherwise, the shirt is styled exactly like his dress shirts for work with its double cuffs, front placket, breast pocket, and slim, moderately spread collar.

Don’s slim necktie is silk with a brown silk ground. The tie’s light blue stripes cross R-down-L with a double dark brown “shadow” stripe above each one. The light blue keeps the look from being too monochromatic and evokes the bright sky and water around him. It’s a smart look.

Maybe it's just me, but Don looks far better than the hippies around him.

Maybe it’s just me, but Don looks far better than the hippies around him.

The Angelico trousers Don wears with his sport coat are taupe with a low rise no higher than the second button on his jacket, an unfortunate decision since the jacket pulls slightly when he has it buttoned and it reveals a bit of shirt and tie underneath. He keeps his jacket on throughout the party (even during his dive into the pool) so not much else is seen besides the belt loops, slanted side pockets, and plain-hemmed bottoms. The slightly flared bottoms (and I mean slightly) are the only sign of the approaching decade in Don’s wardrobe. His slim leather belt is dark brown with a rounded rectangular gold single-prong buckle.

Don’s tassel loafers are also dark brown leather. It’s a good thing he’s far from Bert Cooper’s office because he wears the loafers without socks.


I’d walk away from this conversation too, Don.

Returning from his trip to Hawaii are Don’s space age Ray-Ban Olympian sunglasses with their curved gold rectangular frames and wide dark green lenses. I’m grateful to BAMF Style commenter Johnny for indicating that these are actually the Olympian II Deluxe frame, which have slightly more squared-off lenses than the more ovular Olympian I Deluxe sunglasses that Draper wore for the season opener set in Hawaii.

The Olympian is no longer produced by Ray-Ban, but Old Focals wisely saw that any Mad Men product would soon be in demand, so they produced the “Draper” model as a nod to the character. The Old Focal Drapers are 5.75″ wide with 2.5″ wide lenses that are 1.5″ tall.

Don’s left hand is rarely out of his pocket (seriously!) so it’s tough to see if he is wearing his iconic stainless Omega Seamaster Deville on the black crocodile strap. The elegant Seamaster Deville was a luxury watch before the Seamaster was positioned as a diver’s watch, but one hopes that the water resistant 34mm case would have withstood Don’s unwise late night, hashish-induced swim.

Go Big or Go Home

…or go for a swim!

Don isn't as prepared for this dip in the water as he was when he was in Hawaii in the season premiere.

Don isn’t as prepared for this dip in the water as he was when he was in Hawaii in the season premiere.

Don and Roger complain about riding in Harry’s ’66 Ford Mustang…

Don: There’s no one from GM in Los Angeles? Get rid of that car!
Roger: And get us something with a roof. I don’t want to show up to a meeting with bugs in my teeth.

…but I think Don’s primary concern is knowing that he’ll look too cool. Frankly, no one in their right mind would complain about riding around southern California in a candy apple red Mustang convertible on a hot summer day. This particular Mustang, with its “pony” interior, was lent to the production by Classic Auto Rental Services and powered by Ford’s 289 cubic inch “Windsor” V8 engine.

Like any good party hostess, Harry’s friend Cindy has music ongoing during her Hollywood bash, all from 1968, including songs you’ve heard before (Jeannie C. Reilly’s “Harper Valley P.T.A.”), songs you may have heard before (The Leaves of Grass’s “All This is Right”), and songs you probably haven’t heard before (“Electric Hand” by Pretty).

In the spirit of 420, this party also marks Don’s first experience with hashish. After responding “I don’t know yet,” to a PYT asking if he likes it, he coolly takes a puff, nodding his approval with such a masculine assurance that the drug lobby had to be pretty thrilled with this episode.

Draper takes a hit of some evidently good shit.

Draper takes a hit of some evidently good shit.

Of course, his subsequent reaction and out-of-body dive into the party’s swimming pool would not have been greeted as enthusiastically.

How to Get the Look

Seriously, Don? It's a Mustang. Quit complaining.

Seriously, Don? It’s a Mustang. Quit complaining.

Headed to a party this summer? If you care about making a good impression (whether you plan on getting high or not), Don provides a relatively easy example for you to follow. Just make sure you actually pack swimming trunks if you plan on heading into the pool.

  • Cream raw silk single-breasted 2-button sport coat with notch lapels, patch breast pocket, patch hip pockets, 3-button cuffs, and double rear vents
  • Light ecru dress shirt with slim collar, front placket, breast pocket, and double/French cuffs
  • Brown silk necktie with light blue R-down-L shadowed stripes
  • Taupe flat front low rise trousers with belt loops, slanted side pockets, and plain-hemmed bottoms
  • Dark brown leather belt with rounded rectangular gold single-prong buckle
  • Dark brown leather tassel loafers
  • Ray-Ban Olympian gold rectangular-framed sunglasses with dark green lenses
  • Omega Seamaster Deville wristwatch with stainless 34 mm case, textured black crocodile strap, and black dial with date indicator

Do Yourself a Favor and…

Check out the sixth season.


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  2. J0hnny

    I believe he is wearing a Ray-Ban Olympian II Deluxe, with squarish lenses.

    For the season premiere, The Doorway, it’s a similar model, Ray-Ban Olympian I Deluxe (slightly more oval lenses).

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