Dress Like the Mad Men: the Style of Roger Sterling

The Styles of AMC’s Mad Men – Menswear of the 1960s

Who ever thought the 1960s would be so cool? With the success of AMC’s “Mad Men,” tight-fitted gray suits and crisp spread collars are suddenly getting a second look.

There’s more going on than a simple “man in the gray flannel suit” look, however…join us in a series of articles taking an in-depth look at each of the Mad Men’s personal style!

In the offices of Mad Men’s Sterling Cooper (and later Sterling Cooper Draper Pryce), Don Draper is the modern man — sharp-looking, understated, and timeless.

Roger Sterling, in contrast, dresses impeccably and consistently in older and sometimes flashier fashions, mixing classic cuts with colors and patterns that suit his bon vivant lifestyle within the boundaries of business wear.

Mad Men Suits: Double-Breasted and Vested Jackets on Roger Sterling

As an old hand in the advertising business and a military veteran, Roger Sterling is an understandably crisp-looking gentleman when he dresses for success.

The fit of his suits is usually tighter than his fellow Mad Men’s, with higher armscyes (the hole where the sleeve meets the jacket) and less padded shoulders

Sterling's close-fitted suit, next to Draper's looser cut.

Sterling’s close-fitted suit, next to Draper’s looser cut.

The most striking feature of Sterling’s wardrobe, of course, is his dedication to the double-breasted jacket and single breasted suits with a vest. There’s more to these outfits: more cloth, more buttons, and more formality as well.

Since the effect of all that visual weight can be stifling, Sterling is careful to lighten the suits up with lighter colors or pinstriping on the darker suits. The lighter threads keep him from seeming weighed down by the volume of the suit (his tight fit also helps here, keeping him from swimming in excess fabric).

Roger Sterling and Don Draper wearing light grey three-piece suits

Lighter colors help keep the vested suit from looking stifling.

Sterling is also the only Mad Man who regularly sports peaked lapels. The flaring, upward-pointing style has a dramatic effect, especially in a room filled with men wearing the more conventional notched lapels. Some of his peaks are more dramatic than others — the wider and more flared they are, the more lively they make his appearance, giving a good indication of the hard-drinking party-lover beneath the business suit.

Roger Sterling in a pinstripe suit with peaked lapels

Aggressively peaked lapels give Sterling a very striking appearance. The pinstripes keep the visual impression light.

At other times, Sterling opts for a peaked lapel that merely sets his suit apart from his co-workers’. Either way, his double-breasted jackets with their sweeping lapels are a more dated style than the younger men’s 1960s sack suits — and more elegant, in keeping with his gray hairs and experience.

Roger Sterling in double-breasted suit

Classic elegance in the workplace — and in light colors once again.

Roger Sterling’s Shirts: Collars and Neckties the Mad Men Way

All the Mad Men wear white shirts on the job. That was the business standard in their time period, so the variation is subtle. That doesn’t mean that it’s absent, however — the shirts that Roger Sterling wear are very different from Don Draper’s or Harry Crane’s.

Remembering that Sterling is older, wealthier, and at heart a bit flashier than most of his firm, it’s no surprise that he usually eschews the business-standard point collar. A few appear in his wardrobe, but he’s the master of the varied shirt collar at Sterling Cooper: spread or “cutaway” collars, rounded club collars, and even pin collars with a metal fastener show up on Sterling’s neck at one point or another.

Roger Sterling in three-piece suit

A metal collar pin is definite “dandy” fashion – but elegant with Sterling’s polished look.

Sterling’s varied approach to collar styles is certainly something he can indulge in because he’s already at the top of the food chain. He doesn’t have to play things safe the same way that an employee looking toward advancement does.

His ties play out along similar lines: from time to time, a narrow, solid-color tie crops up in Sterling’s wardrobe, but day to day he’s the master of the figure patterns. Most of his ties feature a repeated pattern that is more complicated than a simple repeating stripe.

Highlights include a navy tie with white “stars,” various polka dots and diamonds, and a few prints that look very similar to some of the art nouveau wallpapers featured in some of the show’s interior.

Roger Sterling wearing pale green floral tie

Pale green floral patterns — you could put it on your wall no problem.

What you don’t see around Roger Sterling’s neck are bright colors of any sort. There are light colors, which are particularly distinct when paired with a dark suit, but he does not wear reds or oranges or anything with a deep and vibrant hue. He also tends to avoid pairing monochrome ties with monochrome suits, or any kind of subdued pattern with a lightly-patterned suits.

When he wears a pattern, it’s usually larger and more shaped than anything that might appear on a suit jacket. This keeps his tie from coming too close to matching his suit. If the colors and patterns ever became similar but not quite matched, he would look like someone trying for perfect symmetry and failing — Sterling avoids the danger with his intricate figure patterns.

Roger Sterling and Don Draper at a bar

Polka dots are also just plain fun.

Pocket Squares and Shoe Shines: Fashion of the Mad Men Stars

Roger Sterling’s Pocket Squares

Neither Roger Sterling nor Don Draper likes to wear a suit without a pocket square. In the world of 1960s Madison Avenue, the pocket square is one of a very few personalized accents permitted by the business dress code, and they take advantage of it.

Don Draper’s consistent horizontal fold is fantastic characterization: he wears a pocket square to show that he cares about his appearance beyond simply wearing the minimum requirement, but refuses to define himself by sporting an elaborate and unique style.

Roger Sterling, in keeping with his changing ties, different collar styles, and fancy cuts of suit, wears differently-styled pocket squares to suit his mood. At his most formal, he’ll opt for a subdued horizontal fold as well:

Roger Sterling in a suitAround the office, however, Sterling often folds his pocket square with multiple peaks, creating a very affected style indeed:

Roger Sterling inside a carThree peaks here — sometimes it’s one, sometimes it’s two.

The key thing to note is that the style is always changing. Just as with his collars, his suits, and his ties, Sterling is not afraid to shake things up. He’s in charge, he has no one to impress but the ladies, and he has years of sartorial experience on most of the other Mad Men (excepting the ancient and eccentric Bertram Cooper), and he makes sure that no one forgets it.

Shoes Make the Mad Man

It’s a minor note in some ways, but it’s worth recognizing that Mad Men shows us more of Roger Sterling’s basic fashion maintenance than most of his fellows’. We see him at the barber’s and at a shoe shine stand over the course of the show. He’s serious about both those stops — these minor chores are part of the serious business of being Roger Sterling.

Both are also business opportunities, or at least the opportunity to stop and talk to a business partner, but is it really concievable that Roger Sterling would go long without either visit?

Roger Sterling getting his shoe shined

This is clearly part of the routine for Roger Sterling — and the ribbed black socks match the dark pinstripe trousers.

Stylistically, it’s hard to fault Sterling’s choice in footwear. The soles are perhaps a touch thick by 1960s standards, but actor John Slattery isn’t quite as tall as Jon Hamm (Don Draper). In fact, he’s probably wearing lifts inside the shoes as well, strictly for production needs — Slattery is at least two inches shorter than Hamm, viewed off the set.

But the plain, black Oxfords with straight-horizontal “bar” style lacing is very professional, and a glance at Sterling’s ankles shoes us that he properly matches his hose socks┬áto his trousers, not his shoes.

Roger Sterling’s Style in Mad Men Terms

So what would one of our image-conscious Mad Men have to say about Roger Sterling, or about any man that emulates his style? First and foremost, this is a wealthy, powerful man with time and cash to spare on clothes that stand out. He’s also business-savvy and a touch old-fashioned — nothing about him is loud or pushes the boundaries of appropriate menswear for the corporate world.

When he sets himself apart from the crowd, he does it by paying attention to details (elaborate pocket square folds, etc.) and by reaching back in time for unusual styles (double-breasted and vested suits, peak lapels, dark pinstripes).

There’s also a touch of the bon vivant, the party animal. Sterling’s ties are perfectly proper, but they’re livelier than some of his fellow Mad Men’s. His changing style in general is part of the same idea of a restless, larger-than-life man.

Sterling can’t be tied down to a single collar or cuff, a particular hat or coat, or anything at all that’s completely consistent. He craves change in his clothing as much as in his love life, and he approaches it with the same reckless abandon. A man could do worse…

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About Antonio

Antonio Centeno is President of ATailoredSuit.com and the founder of RealMenRealStyle.com. He has created over 700 articles & videos on men's style, blogs over at the Art of Manliness, and is the creator of the internet's best selling personal presentation course - A Man's Guide To Timeless Style. Antonio has studied clothing design in London, Hong Kong, and Bangkok. He is a former US Marine with an MBA from UT Austin and a BA from Cornell College. He loves to hear from old friends and make new ones.