End The Madness: Esquire Calls Don Draper An Undertaker


Since it first aired in 2007, “Mad Men” has been the point of origin of a nostalgic zeitgeist for all things mid-century. From hotels to haircuts, from two-inch ties to tiki bars, an infatuation with the so-called “Mad Men Era” has permeated fashion and design.

Now the trend may finally be reaching its inevitable end, at least according to Esquire Magazine.

A few days ago, Esquire’s Style Blog posted the above photo, a promotional shot for the show’s upcoming season, accompanied by an interesting bit of style explication, comparing Roger Sterling’s “acid-drenched swinger” look to Don Draper’s drab ensemble:

This juxtaposition perfectly illustrates the direction of contemporary menswear. Roger Sterling’s look isn’t just cool for 1968 – it’s actually perfect for spring 2014. With a peak lapel, double-breasted blazer, plaid pants, and Chelsea boots, he looks alive and ready for the future, while Don looks – well – like an undertaker. Draper’s slim suit featuring affectations like like tie clips and ironed pocket squares is giving way to a looser, freer look . . .

Calling Don Draper drab and dated is significant, considering that only a few short years ago the fashion press routinely used the character as a metonym for sleek, monochromatic minimalism in menswear. Tie bars and pocket squares in the “TV fold” were the next “must-have essentials” for any well dressed man, and new generations were introduced to Brylcreem and the side part. Now, as menswear edges away from Americana and looks to Italy and Japan, those totems have fallen.

Even more telling, however, is that the newest season of “Mad Men” takes place in 1968, the year in which the decline of the Ivy Look reached its conclusion. In light of this, the correlation between 1968 and 2014 is a strong one, as we are witnessing another decline of an Ivy influence in men’s fashion. — ZD

20 Comments on "End The Madness: Esquire Calls Don Draper An Undertaker"

  1. An interesting comentary, but not one I’d personally agree with.It doesn’t help that the wardrobe department insist on putting Jon Hamm in suits about 1 size too small for his broad frame. As we all know, fashion comes and goes…However, the appeal of a perfectly tailored suit, no matter its affects, will never fade. However, I’m glad I didn’t ditch all my suits with pleated pants….as something tells me that they will soon be vouge again.

    Though, if this signals the end of the ultra slim fitting (alpha sized)craze abounding in most menswear quarters, then I’d gladly welcome it…it would be nice to buy a pair of pants that actually fit again.

  2. I am really, really, really, tired of the way this TV show completely dominates the way people think about what men wear.

    Every time I hear from someone that I or anyone else has a “Very Mad Men Look” I can only think about how they are trivializing (not that clothes aren’t already trivial enough) a man’s appearance by basically telling him that he is wearing a prop from a costume department.

  3. Esquire, GQ, etc., where the contempory styled pretty boys, gain their fashion sense!!!

  4. Preposterous. I suppose we are only a few seasons away from butterfly collars, as well.

    I’ll be staying with the classics.

  5. I’ve read that the posters and promo shots usually offer a preview to the upcoming season. He’s probably in the dark suit on purpose. And it looks like Don is going to a dark place in this final season. Maybe he finally snaps out of it in the end, but for now, he’s probably the biggest mess on Mad Men (eg; jettisoned by the company, wife hates him, always lets down the kids)

  6. The decline of the Ivy look in 1968 did not lead to the disappearance of OCBDs, khakis, gray flannels, reppe ties, Weejuns, blazers, or tweed jackets in the ensuing awful years. I think that what we’re seeing now is not a decline in Ivy influence, but a decline in outlandish preppy influence. All of the items mentioned above are available, and, I predict, will continue to be so into the indefinite future, as long as there are those who want to dress like gentlemen.

  7. A man can establish his own style or chase fashion.

  8. Neither of the characters pictured here ever dressed Ivy on the show, so the tie-in to Ivy’s decline is difficult to discern.

  9. The simple truth is that Mad Men have jumped the shark.
    Early 1960s were a great period to regret,1968 no.

    A sleek, monochromatic minimalist man in 1960 near to others monochromatic minimalist men is elegant and cool.
    in 1968 near to garish and tawdry playboys and long hairs hippies is sad.

  10. The 1960s decade was a bipolar one, with the first seven years vastly different from the final three. Unfortunately, when most people hear the term ‘sixties” they usually visualize only the final third of the decade with its long hair, psychedelia, earth tones, “mod” clothing, love-ins and lava lamps.

    A great aspect of the previous seasons of Mad Men was that it showed the masses what the greater part of the decade actually looked like.

    Now that the show enters its final arc, I imagine the characters will be displaying more and more of the late-60’s unfortunate aesthetic shift as the season progresses.

    As depicted here, Roger is not being overtly cutting-edge for 1968; I was wearing his exact same outfit (except for the shoes) in the fall of ‘66. I am not sure why this look was referred to “acid drenched.” Except for the shoes the look is fairly classic, particularly ideal for enjoying a pre-dinner libation at the bar of one’s yacht club.

  11. Mod clothing originally dates from the late 50’s to the mid 60’s. It was very influenced by Ivy, via Miles Davis, Booker T. & The MG’s and the Blue Note artists, whose record sleeves mods obsessively examined until they got the exact look with their OCBDs, 3-2 rolls, narrow repp ties and bass weejuns.

    It has a lot more in common with Ivy than with psychedelic or hippy looks. From 1967 onwards it gradually disappeared from the mainstream and became a cult thing which has survived to this day.

    Fortunately, nowadays fashion trends aren’t as massive as in the 60’s and 70’s. Style is a lot more individualistic now. Today you can have a neat haircut and wear a 3-2 roll navy blazer and grey flannels, or have long hair and a beard and wear denim or have a shaven head and an ultra-fashion suit and nothing looks out of place.

    That’s why I think Ivy style will never disappear. Fashion trends will be more or less influenced by it, but it will remain, with some variations now and then, a timeless style.

  12. The point of origin of a nostalgic zeitgeist for early 60s is not “Mad Men”,but movies as “Down in Love” and “Catch me if you can”.
    “Mad Men” is the apex of the trend.
    The problem is that the show moved quickly from early to late 60s.
    In late 60s the magic is all gone; was a depressing,unwholesome period.
    1968 was a damned dark,gloomy,terrible,year !

    Anyhow i’m not to said farewell to the skinny suits trend ( a sick and degenerate version of 60s men fashion),but I would not that the next trend is a baggy revival of the worse 80s.
    Or the return of 70s very big lapels and tie!
    Maybe is necessary a new successful TV series set in Park Avenue on the cafè society of 50s.

  13. DB McWeeberton | March 21, 2014 at 12:22 pm | Reply

    The key to understanding this photo is in understanding the background of the characters:
    Don is always in disguise as a normal, mainstream American businessman, hence the conservatism of his wardrobe. Roger was born rich and entitled, so he has nothing to prove, so he’s always Roger, a man who can do whatever he wants. He’ll embrace the late 60s peacock look and any trendy movement that appeals to him. If he doesn’t die of a heart attack, he’ll have a big mustache and flares in the early 70s.

  14. I don’t recall anyone wearing the DB navy with plaid pants and the high shoes in the late 60’s. Around 1970, that kind of stuff was seen in stores, but rarely worn. Some very young men wore the “mod” look, some of the rock stars of the era did before the hippie look took over.

    Only a jerk like Roger would wear an outfit like above in 1968. Back then, most everyone looked like undertakers. Hope the stewardess dumps the drinks on Roger. He looks like he has it coming.

  15. You get on a plane and sit next to a Roger or a Don. With Roger you get plaid pants, boots and ,most likely, have to contend with air heavy with cologne. (Could there be a gold chain on his wrist hidden by his monogrammed cuff?) You know Roger is going to talk from take off to landing and you’ll need a couple of Scotchs to survive. With Don (undertaker?) you get a good conversation and maybe some work contacts worth pursuing down the road. Sure Don is a bit snotty, but he’s also to be taken seriously. Roger is a joke. Clothes tell a lot about a man, especially a business professional.

  16. @ RC

    I worked with a fellow in the 1980’s, who must have dumped a bottle of cologne on himself every day. You could smell the heavy cologne he wore before he rounded a corner. I’m not joking.

  17. Roger looks ridiculous. Those boots are the worst. Esquire has zero authority to me now.

  18. The Esquire article starts off as an interesting commentary on the wardrobe in the latest MM tv series. But then things go downhill with usual picture of a young model in an absurd outfit, here a guy wearing a blazer with pyjama bottoms. How does that publication expect to be taken seriously?

  19. Esquire became irrelevant many decades ago.

  20. It sure would be nice to have that kind of legroom in an airplane. Yes, I know that has nothing to do with style.

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