The Definitive Mad Men Style Ranking

Style Lists Mad Men
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Though hard to believe only a mere seven seasons ago the world was introduced to the likes of Sterling Cooper Pryce, the fact remains AMC’s Mad Men is drawing to a close. While a lot has changed for all involved: the company name for one, the players for two and hemlines and sideburn lengths for three, the fashionable aesthetic has remained a constant and practically an eleventh character. Whether it was 1960s cupcake party dresses or the British Invasion with its mod connotations, even the rise of the hippie, Mad Men captured each distinct era and breadth of style therein, sparking a resurgence of menswear and a push for vintage kitsch today, making yesterday’s looks new again.

As the final season winds down and everyone ponders where their office favorites will end up after all is said and done, we here at Paste have created our own list of who wore what and who wore it best.

Honorable Mention: Stan Rizzo

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Not one to stand shy in the corner, art director Stan Rizzo was one of the first to adopt an in-office beard, do away with his suit—opting for suede fringe—and wear caramel corduroys like nobody’s business. His mildly rebellious nature may irk Peggy Olson every now and again, but, as a team member, Rizzo not only has a defined, creative style, but an honest nature. And really, if anyone is able to pull off the New York City ad agency meets upstate hippie vibe, Stan is the man to do it.

10. Meredith

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Without the front desk girls and secretaries, Sterling Cooper Pryce would be a completely different office—one without its beloved dynamism, frustrated tension and forget about those insatiable office politics and riotous holiday parties. While each woman brings her own spark to SCDP, Meredith stands out with her knack for ditzy discourse and doe-eyed stare, but do not be fooled by this wolf in a sheepskin coat. Her ability to keep everyone on task, even Don, rivals only one red-headed office maven. Meredith’s uniform veers towards babydoll silhouettes, go-go boots and a half-pony princess bouffant. With her keen eye, there is a lot more to Meredith than she seems to be given credit for.

9. Bertram Cooper

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With his affinity for East Asian design and patterned bowties, Bertram Cooper, a.k.a. Bert, has finagled his way into the top ten. A member of the old guard with a penchant for suits and sweater vests, socks only in the office, demands respects. Even when he appears a tad aloof to the office goings-on, Bert knows all. And, while it was sad to see him go, the classy, musical send-off was everything we have come to expect from the man behind the curtain.

8. Jane Sterling

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Jane Sterling, neé Jane Siegl, was all about the drama. Whether evidenced in her dress and taste for jewels, pearls and structural hats, or in her dealings with Joan, Don and Roger, Jane was the show’s Elizabeth Taylor: a sense of finesse and high couture with a little kookiness stitched in the seams. With luscious locks and an appreciation for one-piece jumpsuits, Jane’s vibrant energy certainly stirred the pot. Though her and Roger’s marriage did not last through their LSD-fueled haze, Jane always dressed the part of a younger wife magically and stopped the presses with her side-eye like a pro.

7. Peggy Olson

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Though everyone rags on Miss Olson’s fashion sense—ahem, looking at you, Joan—Peggy definitely wins our vote for Most Improved. This former secretary has come a long way from mid-forehead fringe and shapeless frocks. Peggy is the epitome of a career focused creative: more and more self-assured, but still wide-eyed in the matters of love. If the eighth episode from season seven hints at anything, Peggy Olson is sure to wow in her contrasting checkered dress suits and contrasting chiffon scarves. Get ‘em, Peggy! You go!

6. Don Draper

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Dapper Don. Draper to some, Dick to others, Don Draper brought back menswear in a huge way. Whether in his work uniform—sharkskin grey—or going for a more casual vibe in California with chinos and polos, Draper always looks sharp no matter what existential crisis plagues him at that precise moment. Always a classic, Don Draper toes the line and consistently looks simple, crisp and ready for wherever and whomever the night throws his way.

5. Betty Francis

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Betty Francis, formerly Draper, may be the ultimate ice queen, but there was a time when she was able to melt even the coldest of hearts. When Betty was Bets, her life and dress were pristine to most, with only a few allowed a glimpse of the sloppy, angry woman beneath. Though her character has evolved over the course of the show, with seesaw weight changes and a growing stately appearance, the image of Betty shooting down her neighbor’s pigeons in a pastel pink dressing gown is how we will always remember this complicated dove.

4. Megan Draper

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Megan Draper may not have made quite the splash as Miss Megan Calvet the secretary, but when Don slipped that ring onto her finger, the second Mrs. Draper made sure she controlled the room’s attention—even as Don’s began to linger. Who can forget “Zou Bisou Bisou” and her butterfly-sleeved black mini? Or when she got all Valley of the Dolls Sharon Tate on us after moving to California? As the antithesis to Betty, it was fun to watch Megan put Don through his paces but ultimately both women ended with the same result. At least Megan won the sun and the beach, groovy head wraps and bellbottoms.

3. Roger Sterling

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Roger Sterling is the man of one-liners, scotch before ten a.m. and finesse. The only subtle aspect to Roger is his dress. He outshines Don Draper when it comes to taking understated suiting risks—i.e. a three piece with watch chain or adeptly folded pocket square. Even when Roger went through his LSD, trippy phase, he did not buy into the psychedelic duds of his counterparts, though he has been known to experiment with sideburn length and most recently, facial hair. No, Roger will be buried in a three piece suit. Let’s just hope he shaves the ‘stache sooner than later!

2. Joan Harris

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Joanie has always been a vision in the office, no matter the name on the wall or her title. With brilliant red locks and a calm demeanor, Joan proves sense of style is all about attitude. Her closet standards, while always work appropriate, tend to have a bit of sass woven through. Whether a hot pink dress or layered necklaces, Joan adds a zippy pop to any outfit and much like her blunt assessments of the office’s goings-on, her bold ensembles, with a touch of prep, make a statement no one is bound to forget any time soon.

1. Sally Draper

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All hail Miss Sally Draper! Not so much a rags-to-riches story as a rebellious teen finding her voice, Sally won our hearts with her blunt wit and tartan frocks. Now she has swapped her saddle shoes for go-go boots and is primed for life as a teen during the ‘70s. Her eyebrows are to die for, and whether she throws on a plaid poncho or single strand, gold chain, Sally has the whole world wrapped around her finger and growing style to match. Needless to say, we have always been Team Sally Draper.

Have a different ranking in mind? Let us know in the comment section below.

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