Mad Men – “Three Sundays” Sweater

Jon Hamm as Don Draper in

Jon Hamm as Don Draper in “Three Sundays”, Episode 2.04 of Mad Men.


Jon Hamm as Don Draper, brilliant Madison Avenue ad man

New York City, April 1962

Series: Mad Men
Episode: “Three Sundays” (Episode 2.04)
Air Date: August 17, 2008
Director: Tim Hunter
Costume Designer: Janie Bryant


Face it, even when he goes in on the weekend for his day off, Don Draper will look better than you. And this isn’t just a statement about the times: he also looks far better than Pete Campbell in his monochromatic tennis gear and short shorts.

This episode of Mad Men, the fourth of the second season, is centered around Sterling Cooper’s campaign to win American Airlines as a client. Don is on the verge of both a professional and a personal crisis but manages to hold everything together, crafting what he believes will be the perfect pitch.

If you have no idea what I’m talking about or who these people are, watch the damn show already. If you’re more of a cheater, read my first post about Don Draper and maybe you’ll have a slightly better sense about what’s going on.

What’d He Wear?

Responding to the emergency call of working on a weekend, Don shows up at the office in the epitome of suave 1960s male casual wear. While everyone else’s attire is hit or miss (Hit: Ken Cosgrove nicely wears a light brown sportcoat and tie. Miss: Pete Campbell’s aforementioned tennis outfit), Don comes in looking relaxed but professional.

Don Draper to the rescue!

The staple of Don’s every outfit, the white dress shirt, is present here. However, the first thing Don does is roll up the sleeves under his sweater. Whether the shirt has French cuffs or not, this sort of work is no place for decorations: Don came in to work. Like all of his shirts, it also has a breast pocket for the ever-present packet of Lucky Strikes.

Over his shirt, Don wears a dark navy medium weight merino wool sweater with a slight V-neck. According to the 2015 auction listing, the sweater has a Knitwear by Di Fini label.

Draper doesn’t need a gray flannel suit to make one of his trademark brilliant pitches.

Don’s tobacco brown flat front trousers have a long rise, full fit, and plain-hemmed bottoms with no cuffs. The pockets are standard: slanted on each side with two jetted pockets in the back, each closing with a button.

Forgoing his usual laced shoes, Don wears more casual black leather tasseled loafers and black socks on his feet. His thin black leather belt matches the shoes.

The only glimpse we get at Don’s shoes in this scene is when his 8-year-old daughter Sally drops her empty whiskey glass at his feet. Oh, 1962.

On his wrist is Don’s Season 2-3 watch, a gold Jaeger-LeCoultre Reverso Classique with a rose gold case and a brown leather alligator strap.

Seriously, what does he need that globe behind his desk for? What part of advertising requires scale knowledge of the fact that Greenland is actually smaller than it appears on a regular map?

Underneath’s Don’s standard white undershirt peeks through over his open shirt and sweater, reinforcing the relaxed and casual nature of his clothing.

Despite it being the weekend and wearing casual clothing, Don still wears his usual outerwear when going in and out of the office: his usual knee-length 4-button taupe raincoat and dark gray felt short-brimmed fedora with a black band and feathers.

To actually pull off a fedora, wear a classic gray like this one instead of the striped vinyl ones sold at gas stations and as part of “gangster” Halloween costumes.

An interesting facet of this episode is seeing what Don wears when he actually comes to the office to work. Don wears his sharp suits when he is coming to the office for a stellar presentation, the seduction of a client’s wife, or even a nap on his couch. However, when it comes to actually buckling down and working with no distractions (other than a few glasses of Canadian Club to get the creative juices flowing), Don has no time for ornamental clothing. He still looks professional, but he is dressing like a younger generation of people, the ones who need to work just a little harder to get their jobs rather than getting their bosses drunk and showing up the first day (see Season 4’s episode “Waldorf Stories”.)

Go Big or Go Home

As most of America’s offices are “business casual” now, outfit like Don’s sweater and slacks in “Three Sundays” are more common sitting behind a desk, especially in creative firms such as advertising and PR. A lot of people may try to go for the look but will either look like they’re trying too hard or they’ll look like their dad did during a 1994 trip to church.

A lot of people that put a look like this together think too much about having to have a pattern or something that stands out. Why? Get some strong solid colors and see what works.

Another important thing to remember is that Don wore this because it was comfortable and appropriate for his office on the weekend. He didn’t stand in front of a mirror, fussing with accessories and thinking, “Gee, I hope Joan likes this new shirt.” No. He is wearing practical clothing and happens to pull it off much better than the men around him.

Notice how a gentleman like Don Draper still looks at his daughter even when more eye-catching subjects are around.

What to Imbibe

He’s in the office and very busy, so Don doesn’t have any time for frills. Time spent muddling cherries and orange slices for an Old Fashioned is time wasted. Then again, so is time getting ice. Pour a few fingers of Canadian Club into a rocks glass – no rocks needed – and let the brilliance flow.

Don doesn’t let things like “Work” or “Being at the office” interfere with his usual weekend agenda.

How to Get the Look

There’s a very good chance you already have the bulk of these items, so that ought to make this easier:

  • White cotton dress shirt with a moderate spread point collar, breast pocket, and double/French cuffs
  • Navy-blue merino wool sweater with a slight V-neck
  • Brown flat front slacks with belt loops, slanted side pockets, button-through jetted rear pockets, and plain-hemmed bottoms
  • Thin black leather belt with small gold buckle
  • Taupe single-breasted beltless 4-button raincoat with a long single vent
  • Dark gray short-brimmed fedora with a wide black band and brown/red feathers
  • Black leather tasseled loafers
  • Black dress socks
  • Jaeger-LeCoultre Reverso Classique wristwatch with a rectangular yellow gold case and brown alligator leather strap
  • White short-sleeve crew neck undershirt
  • White cotton boxers

Do Yourself a Favor and…

Check out the second season.

The Quote

There is no such thing as American history. Only a frontier.


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