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