Mad Men Style - Roger Sterling

Mad Men Style: Roger Sterling

Luckily for us, AMC’s hit show Mad Men is a deck thickly stacked with classically dressed male characters. Don Draper, the show’s emotionally complicated and charismatic main character, is often aided and abetted in his behaviors by Roger Sterling, the man who originally spotted Don’s diamond in the rough. Today, we will focus on the character of Roger Sterling and his wardrobe.

Roger Sterling’s Character in Mad Men

Mad Men Season 4 Cast

Mad Men Season 4 Cast

At the onset of the show, Don is Sterling’s employee, but he eventually rises to his equal at the new firm Sterling Cooper Draper Pryce. The two characters share many similarities – ambition, panache, and of course a penchant for women who are not their wives – but sartorially speaking, it’s clear that Don and Roger come from two different style generations.

In 1965, Don is 40 and was too young to fight in WWII. Roger, a WWII vet, is certainly older, though his white hair can be misleading – actor John Slattery Jr. is only 50 years old. Regardless of his exact age, Roger became an adult in the late 20’s and 30’s, while Don would have formed his early style preferences in the 40’s and 50’s. It seems that after suffering as an adult during the depression, Roger has an appreciation for fine things, and as such he chooses a three-piece suit to be his signature combination. Having inherited his role at the firm and the now-defunct legacy account of Lucky Strike cigarettes from his father, Roger has never really had to do much around the office.

Roger Sterling with Vest Only

Roger Sterling with Vest Only

He clearly has some entitlement issues, which often manifest themselves in the form of sarcasm, crudeness, and overindulgence. Roger has yet to really learn from a mistake, and his choice of dress acts as the façade of his all-show and no-action behavior.

Clothes of Roger Sterling in Mad Men

Almost all of the suits Roger wears in Mad Men are 3-piece suits with pleated, cuffless trousers. The double breasted suit aside, the classic three-piece suit is as dressed up as one can get before encroaching on evening wear, and it’s well suited to his egotistical personality. Given his age, Roger is more set in his ways, and is unlikely to appreciate the style direction the 60’s has taken. The fabrics he chooses are all rooted in business attire, and range from light gray worsteds, navy serge and charcoal shadow stripes to fine pin striped suitings. Outside of the office, he usually wears a hat paired with a topcoat and  classic black oxford shoes. Throughout the show, his shirts are almost exclusively plain white –an affinity shared by most of the male characters.

Inside the Car

Inside the Car

Within the range of clothing items that Roger deems acceptable to his image, he demonstrates much more willingness to play with different style components. For example, you can see him in various shirts collars, with or without a collar bar, various ties and accessories such as flat, golden wrist watches, pinky finger rings and cuff links. His ties, while not overly wide, are never as narrow as Don Draper’s ties and are much more classic at about 7 or 8 cm in width. Also, he wears varying pocket square fabrics and folds – crowned, flat or simply puffed. His favorite accessory is obviously the cigarette, with a close second being the lowball glass.

Despite his attention to detail, he commits the occasional faux pas that seems more attributable to the costume designer than it is to his character’s choice. Sometimes, you can spot him wearing a tacky matching tie and pocket square combination that a man of his confidence would not need to stoop to wearing. Even worse, you can often see him wearing a belt underneath his vest, which causes it to bunch up and reveal the low rise of the pants and a usually-hidden puff of shirt fabric.

Bert Cooper in Argyle Socks & Roger Sterling

Bert Cooper in Argyle Socks & Roger Sterling

He always wears single breasted coats with notched lapels, typically with 3 buttons. His matching waistcoats are likewise single breasted and he always follows the rule of leaving the bottom waistcoat button unbuttoned. But let’s take a detailed look at one of Roger’s outfits:

Here, Roger wears a shadow-striped, charcoal suit with white shirt, beige and black dotted tie, with a matching pocket square and cuff links. Instead of pick stitching and real buttonholes, the coat features a machine sewn edge and 4 cuff buttons. While this was in fact seen in 1960’s upscale suits, as Roger would have worn them, they would have had proper pick stitching and hand sewn buttonholes.

Roger Sterling Details

Roger Sterling Details

The charcoal shadow stripe socks are combined with black half brogue oxfords that don’t seem to fit him particularly well. Also, if you pay attention to the way his shoes are laced up, you notice that neither of his shoes are laced up in the proper oxford pattern of parallel lines. Amazingly, both shoes have a different pacing pattern! Considering this is a classic outfit, no business man in his right mind would have laced his shoes in two different ways.

Roger Sterling Oxford Shoes

Roger Sterling Oxford Shoes

This lacing pattern occurs throughout the Mad Men seasons, which makes me believe they only had him wear a single pair of shoes throughout the entire show!  Suffice to say, you should always rotate your shoes in order to get more wear out of them and of course, for the sake of elegance, it’s desireable to have a variety of shoe patterns. Having only one pair of go-to shoes – even if they are a versatile classic such as Roger’s black oxfords – still creates an ongoing compromise of style. They will never be a perfect match for all outfits, and it seems unlikely that a man who appreciates his accessories in the way Roger does would only wear one pair of shoes.

Overall, Roger Sterling is an important character in Mad Men. He has some of the best lines lines and his character is well supported by his wardrobe, with the exception of his shoe and belt selection.

What do you think about Roger Sterling’s outfits in Mad Men? Let us know!

5 replies
  1. richard
    richard says:

    thanks for this installment, raphael

    lowball glass and cigarettes-a whole new approach to accessorizing! the lacing discovery is classic; maybe he’s pre-grunge.

    hopefully you can focus some attention on sal romano, who i believe was written out at season-end of the fourth year. i recall he definitely pushed the envelope; alot of color and rarely seen in black shoes. in fact, he gives historical credibility to the current ‘brown is the new black’ mantra. it’s quite possible that being one of the creative staffers with minimal client interaction, he would be more willing to experiment with fashion at the time.

  2. richard
    richard says:

    yes, he’s got that european deal going on, but there is some predictability in his choices. like to see him head home, spend a big bonus check, and come back to new york with a real fashion statement.

Trackbacks & Pingbacks

  1. […] comfortable exploiting the wide range of options that a classic wardrobe provides.Roger SterlingRoger Sterling, as you’ve probably noticed, can be relied upon to wear a three-piece suit in the same way that […]

  2. […] back or side adjusters. Vests may be worn with the latter two choices, but never with a belt. See Roger Sterling.Most men look best if they display between half an inch and an inch of shirt cuff underneath their […]

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