AMC period drama Mad Men (2007-2015) received critical acclaim for its innovative storytelling and immersive portrayal of 1960s America. A large part of the show’s success was the beautiful and historically accurate costumes, courtesy of designer Janie Bryant.
Bryant used color, shape, and texture to tell each character’s story, from the suited-up Sterling Cooper executives to the secretaries keeping the ad agency running. No matter how small the role, there was always a story behind the costume. And just as there was a social pecking order in the office, there was a sartorial hierarchy. Read on for the ten best-dressed characters at Sterling Cooper, ranked.
Harry Crane
Harry may not be anyone’s favorite Sterling Cooper employee, but there’s no doubt that he is one of the snappier dressers. Harry sets himself apart from his colleagues with his desire for a Hollywood career. He gets his first big break as the only employee of Sterling Cooper’s television department in Season 2.
In subsequent seasons, he transforms from nerdy chic to Mr. Hollywood, losing the short sleeves and bow-tie for extravagant jackets, wide patterned ties, and sideburns. We wouldn’t say that he changed for the better, but he does look great.
Lane Pryce
As the only British partner at Sterling Cooper, Lane highlighted his background with details and accessories that would have escaped the notice of his fellow partners. He wore waistcoats, three-piece suits, tiepins, suspenders, and vests with unexpected patterns and textures, such as tweed.
These details set him apart sartorially and added to his polite charm. Not to mention, they were a nice break from the basic grey and navy suits the other executives were so fond of wearing. Lane Pryce is absolutely the best dressed among the old guard of Sterling Cooper, displaying impeccable taste and attention to detail.
Ted Chaough
Ted is the anti-Don Draper in many ways. He wears brown, mustard, and green – the “icky” colors of the late 1960s – with confidence, while Don likes to stick to his classic neutrals. While Don’s color palette is all about mystery and seduction, Ted’s is warmer and more inviting.
The difference in costuming speaks volumes: although Ted and Don occupy the same position at their respective ad agencies, Ted is a younger and more forward-thinking man, by default making him better positioned for success in the modern age. He is comfortable in the fashionable colors of the era, with a yellow, double-breasted sportscoat among his more cutting edge looks.
Peggy Olson
It’s easy to tell whether a scene is from early or late Mad Men. All you have to do is look at Peggy Olson, who started the show in modest plaid dresses and a girlish ponytail. Halfway into the show’s run, the budding copywriter found her sartorial identity with help from the mod scene.
She tweaked her grown-up Catholic school uniform to convey more “business executive” than “secretary” and added touches of pattern and color to showcase her quirky personality and unconventional (for the time) choices in life. It’s clear that Peggy has come a long way, and her efforts earned her a spot on Sterling Cooper’s best-dressed list.
Stan Rizzo
In the 1960s, a significant shift in men’s fashion was taking place. The older generation, like Roger Sterling and Bert Cooper, continued to wear hats like they were taught. Younger men, like art director Stan Rizzo, generally felt that they could do without hats. Stan also did without the standard grey suit. In his first appearance, he wore a polo shirt and leather jacket, signaling his disdain for the suited-up life.
Later on, he wore shirts with Western details and grew out his hair and beard in a nod to the countercultural movements taking hold in the late 1960s. For deviating the most from the conservative Ivy League aesthetic that was so prevalent at the beginning of the show, Stan deserves this spot on Sterling Cooper’s best-dressed list.
Dr. Faye Miller
Dr. Miller is a consummate professional, having the tenacity and competitive spirit to earn her degree in psychology and pursue a career in consumer research at a time when women were discouraged from doing so. She is a fashionable dresser and has the knowhow to use clothing to her advantage.
In the Season 4 episode, “The Rejected,” she changes from a black and beige suit – her usual work uniform – to a bright blue dress in preparation for a focus group with the secretaries. She also removes her wedding ring, hoping to make herself more relatable to the young women she was trying to interview. Dr. Miller’s costume is another example of impeccable 1960s officewear, and the blue dress with the eye-catching gold brooch is a stunning look to boot.
Megan Draper (née Calvet)
Megan barely stood out from the secretarial pool when the show first introduced her. Like the other secretaries, she wore a basic sheath dress in a solid block of color and her hair in a basic updo. All of this changed when she married Don and started working as a copywriter at the ad agency. Megan upgraded her wardrobe to show off her new status and cut her hair into a fashionable bob.
Her wardrobe now includes more dramatic pieces, like this polka dot blouse with ruffles. Megan’s style would transform again after her move to Los Angeles, becoming much more opulent – but as an employee of Sterling Cooper, she was the epitome of office chic.
Joan Harris (née Holloway)
For most of Mad Men, Joan wore a sheath dress embellished with a pin and ever-present pen necklace. After Joan was made partner, she began to explore sartorially, expanding her wardrobe to include A-line skirts, floral print, bold jewelry, and a variety of collars and necklines.
She also wore her hair differently; the updo became less sleek and more voluminous. There was a lushness to Joan’s outfits that hadn’t been there before, which showed off her increased responsibilities at the agency. This black skirt suit with severe lace cuffs and collars is an excellent example.
Meredith
Always a source of comic relief, Meredith is possibly the show’s most memorable secretary. After all, she was the unfortunate recipient of Joan’s rage after she was served divorce papers. Aside from that, Meredith is young, chipper, and takes her job very seriously, though she sometimes misreads situations and spaces out on the job.
Meredith is truly a child of the late 1960s, wearing babydoll dresses in bright colors and her hair in a bouffant to highlight her youthful innocence. With her blank stares and lackadaisical flipping through a magazine, it’s hard to read any malice into her actions.
Shirley
One of two black secretaries to join Sterling Cooper towards the end of Mad Men’s run, Shirley also favors babydoll dresses with bold prints and pointed collars, like this red dress in “A Day’s Work.” Shirley makes several appearances in Mad Men, the most memorable being an exchange with Dawn Chambers, where they wryly greet each other with the other woman’s name.
Although she does not get much screentime, her costuming more than makes up for it. With her on-trend minidresses, go-go boots, and natural hair, Shirley is the sartorial MVP of the Sterling Cooper offices.
