Mad Men’s best dressed: The most memorable looks throughout seven seasons

1. Peggy Olson
Best look: The Pant Suit™

Peggy’s style evolution is unparalleled. From being told to stop dressing like a little girl in season two to walking into McCann Erickson like a boss, Ms. Olson has bossed up exponentially, daring to wear prints, menswear-inspired pieces, and this black dress in season six. The only character whose style evolution comes close? Stan. (Which is just another reason why they’re meant for each other.)

2. Trudy Campbell
Best look: Maternity nightie

Trudy’s style is basically represented by her super-short maternity nightie: she has actual fun with clothes. Via bright prints, super-feminine accents, and pops of colour, Trudy’s wardrobe commands as much attention as her personality, proving that you’re not always the weakest one in the room if you’re also the loudest.

3. Sally Draper
Best look: Go-go boots

Once upon a time, Sally Draper was a six-year-old little girl who played in her mom’s dry cleaning bags. Today, she’s a teenager in charge of her mother’s funeral, and Bryant hit her style story out of the park. The turning point, from girl to (almost) grown-ass woman? Sally’s go-go boots that she wore the night she caught Roger and Marie hooking up, illicitly. Adulthood, you guys: with better clothing comes bigger problems.

4. Megan Calvert
Best look: Zou Bisou-Bisou dress

Don loved Megan because she was his opposite: she was young, fun, daring, and had nothing but potential ahead of her (much like her wardrobe), and ultimately, this is also why their marriage failed. However, nothing epitomized that “oh no” realization like seeing Megan sing while wearing a black mini-dress no other guest was hip enough to wear. Don’s world was not hers — girlfriend’s in screaming colour.

5. Joan Holloway (never Harris, BTW)
Best look: The floral dress

A lot of us associate red with Joan Holloway, but she’s never actually worn it during moments of empowerment. (Remember: that famous red dress is Roger’s favourite — she’s never said it was her’s.) So while Joan had the corner market on fitted pieces and brooches for the 1960s, the seventies ushered in a new era. First, she became independently wealthy, and second, she quit her job. That’s why this floral minidress is so important: Joan had worn bold pieces before, but this dress’ cut and pattern were modern. It’s similar more to Shirley’s look than to Joan’s, which represents a huge shift for the woman whose dresses tended to look similar. (Wonderful, but similar.) This also explains why she wore this dress in the episode she finally left.

6. Shirley
Best look: The red minidress

Shirley was too good for the advertising world. And her wardrobe alluded to such, since it was youthful, modern, interesting, and even risky. (Imagine having that many minidresses.) (And I do, often.) Ultimately, Shirley was a walking reminder that style was changing (and so was the world, obviously), and her unapologetic approach to fashion was both welcome and empowering.

7. Betty Draper
Best look: Her blue dress (not that one)

We never actually saw Betty wear the blue dress she was asked to be buried in, so instead we pay homage to the blue satin dress she wore back in season two, during dinner with Don, Bobbie Barrett (we’ll get to her), and Jimmy. Frankly, nobody wears blue like Betty: she’s regal, she’s cold, and her light features contrast the colour perfectly. Which is something she’s also well aware of — even in her darkest moments, Betty’s never dressed less than what the event calls for. (Though her politics-appropriate/less-fun wardrobe of the seventies is why she’s ranked at number six.)

8. Meredith
Best look: The purple babydoll dress

Meredith’s story is perhaps Mad Men’s most victorious. As a former secretary whom Joan once threw a toy plane at, she’s risen through the ranks to become the only person capable of fixing Don’s (old) life. And through it all, she’s never adhered to Peggy Olson’s (or anybody else’s) school of fashion, and plays up girlish pieces, which makes it even better when she’s delivering bad news.

9. Dawn Chambers
Best look: Her blazer/blouse combo

Dawn broke barriers at SC&P and as such, took her job very seriously which was reflected in her clothing. But at the same time, Dawn still maintained her own sense of style, and opted to merge her own interpretation of fashion with typical office wear. Enter: the combination of her pink blouse with a wool blazer. Had this series gone into the late seventies, you know she’d by slaying even bigger corporate dragons.

10. Jane Sterling
Best look: Black and white hat/dress

As a former secretary for the firm, Jane armoured up when she returned to Sterling Cooper to flaunt her marriage to Roger Sterling in front of Joan (and anybody else who was listening). That’s why she opted for a piece that couldn’t be further from mid-sixties office wear: uptown mod, with a black and white hat, alluding to her future of oversize accessories, designer dresses, and gems (so many gems — too many gems). The thirst was real.

11. Helen Bishop
Best look: Pants

The first time we meet Helen Bishop, she’s wearing pants. In fact, Helen Bishop is never not wearing pants. (Minus when she was campaigning for Kennedy — lest we forget.) Were they remarkable pants? Absolutely not. But considering she was the only woman to wear them (minus Betty’s season one and two riding gear and pieces worn by Midge — who we’ll get to), and kept her attire menswear-inspired, she breaks the top 10. (Why? Because she was interesting. And because I’ll never challenge Abby from Scandal.)

12. Dr. Faye Miller
Best look: Blouse/cardigan

Dr. Faye, we hardly knew thee. But what we do know now is this: after her short time working with SCDP, Faye inspired Peggy to change her own style. (Remember: Peggy didn’t come into boss-mode until season five.) Blouses, cardigans, jackets, and skirts were the name of Faye’s game, and as such a figurehead to Ms. Olson, we can thank her for that contribution.

13. Rachel Menken
Best look: Her feathered hat

If she were starring in Romy and Michele, Rachel Menken would have full access to the businesswoman special. In tailored suit-dresses, jackets, and that feathered hat, she brought Don to his knees via her power-centric attire, capping off her run in the fur coat Don hallucinated (before finding out she died). The only downside? We didn’t see more of it. And when Don ran into her with her new husband a few seasons in, she hadn’t really evolved much, style-wise. (Which seems unfair because she owned a department store.)

14. Bobbie Barrett
Best look: “That” dress

Are our feelings about Bobbie Barrett mixed? No. (I didn’t like her, and I’m sorry — though I’m even sorrier Don was such a predator because that scene is terrible to watch.) Especially since her clothes seemed to over-sell her status while anchoring her in the past. (Very fifties glam instead of sixties glam, to be real.) Bobbie was a powerful woman — maybe we can pretend that circa 1970, she’s wearing wide-legged pants (if she wants).

15. Sylvia Rosen
Best look: Black and nude cocktail dress

Much like Sylvia, her wardrobe didn’t have much of a personality — it just seemed to exist. (Which makes sense, because the character simply exists in her husband’s life and then Don’s life for a while.) Her clothes looked okay, but there was nothing memorable about them. Even when Sally walks in on Sylvia and Don having sex, Sylvia’s wearing a simple printed house-dress — which I actually had to Google it, because I couldn’t remember. Sylvia, friend: you deserve better than your husband and your average clothes.

16. Midge Daniels
Best look: Her men’s shirt

It seemed so promising. Midge answers the door in a man’s shirt, she spends the first season in kimonos and wigs, and then it’s over — Don ends the affair, and we don’t see her again. Until she shows up at the SCDP offices (in a dowdy yellow dress and oversize cardigan) asking Don for money to buy heroin. She’s number 16 because she broke my heart. (Un-do it, Matthew Weiner.)

17. Suzanne Farrell
Best look: None, but especially not this

I blame the flower crown for the boring affair between Don and Suzanne. And so should you.