Style Evolutions: The ‘Mad Men’ Ladies Throughout the Seasons

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Betty Draper
Betty Draper
AMC

Season 1, 1960

When we first met Betty, we met a conservative, yet still stylish, housewife. Even though she was better dressed than most of the other women in the neighborhood, the everyday Betty we initially encountered couldn't hold a candle to the glamorous Betty we'd meet in the future.

27
Betty Draper
Betty Draper
AMC

Season 2, 1962

Betty's bold prints and pearls under her collared shirts are just too too chic for us. We love this look.

26
Don & Betty Draper
Don & Betty Draper
AMC

Season 2, 1962

It's easy to imagine this picture-perfect couple fooling everyone into thinking they were happy back then, but we all know that's not the case.

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25
Don & Betty Draper
Don & Betty Draper
AMC

Season 3, 1963

Pregnant Betty looks angelic in white lace, positively glowing next to Don.

24
Betty Draper
Betty Draper
AMC

Season 3, 1963

Who could forget when Ms. Draper went to Italy looking like this and flirted, in Italian, with some men, right in front of Don? It was one of Betty's finest moments on the entire show, and it was a look we won't be forgetting soon.

23
Betty Francis
Betty Francis
AMC

Season 4, 1964/1965

This was when we began to see Betty refining her style to be the perfect politician's wife. Just like everything else Betty wears, it's flawless.

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22
Betty Francis
Betty Francis
AMC

Season 5, 1966/1967

The dawn of Fat Betty saw Mrs. Francis as classy and stylish as ever, even if she was a little less glamorous and a lot less confident.

21
Betty Francis
Betty Francis
AMC

Season 6, 1967/1968

When Betty goes slumming, she dresses for the occasion.

20
Betty Francis
Betty Francis
AMC

Season 7, 1969

Betty plays it super chic on a school field trip with Bobby. So cool, in fact, that things seem to turn a bit icy when her son mistakenly trades her lunch. While she may not be the greatest mother, she certainly has style.

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19
Peggy Olson
Peggy Olson
AMC

Season 1, 1960

Peggy starts the season as a frumpy, relatively clueless girl who isn't so sure of herself, and it shows in her clothes.

18
Peggy Olson
Peggy Olson
AMC

Season 2, 2962

When Peggy took us to church, she did so in her best little girl dress. Even though she looked cute and appropriate, it only felt like part of the Peggy we knew.

17
Peggy Olson
Peggy Olson
AMC

Season 3, 1963

By season 3, Peggy was trying to establish herself sartorially in a way that matched her professional growth, but still wasn't quite at the powerhouse point we've gotten used to.

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16
Peggy Olson
Peggy Olson
AMC

Season 4, 1964/1965

Perhaps Peggy's most iconic fashion moment? The halo hat is the perfect piece for a character like Peggy, and Elisabeth Moss wore it perfectly.

15
Peggy Olson
Peggy Olson
AMC

Season 5, 1966/1967

While her clothes aren't the most interesting here, it's Ms. Olson's hair that we're taking note of here. As she gains power, she gains volume, like a true boss. Also, note Peggy's key to success: the ability to wear a Bitchy look effortlessly.

14
Peggy Olson
Peggy Olson
AMC

Season 6, 1967/1968

This is one of our favorite Peggy looks. There's a real old lady kind of sophistication to this outfit. She feels proper, and in charge, and stylish, and saucy. And she is!

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13
Peggy Olson
Peggy Olson
AMC

Season 7, 1969

Peggy has her look together now: the bold prints and colors, the neat tailoring and the defined shoulders, and, most importantly, girl has found her power hair.

12
Joan Holloway
Joan Holloway
AMC

Season 1, 1960

When we first meet Joan, she's red hot and makes sure it's noticed. Though still office appropriate, her skirts hug her curves perfectly and her signature necklace dangles in an attention-grabbing way. She was husband-hunting after all, wasn't she?

11
Joan Holloway
Joan Holloway
AMC

Season 2, 1962

We love this Joan look -- there's something nautical and oh so sexy about the way she wears it.

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10
Joan Holloway
Joan Holloway
AMC

Season 2, 1962

She pulls off glamour effortlessly, but we already knew that. What we loved about this Joan look was her hair and the asymmetrical shoulder. She looks wise, calm, confident. We love it.

9
Joan Harris
Joan Harris
AMC

Season 3, 1963

Joan takes up the housewife game in such a respectable way. Her dress is completely appropriate for a wife entertaining at home, and her new accessory, that tray, is the perfect finishing touch!

8
Joan Harris
Joan Harris
AMC

Season 4, 1964/1965

Now Director of Agency Operations at Sterling, Cooper, Draper, Pryce, Joan takes no prisoners.

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7
Joan Holloway
Joan Holloway
AMC

Season 6, 1967/1968

We love Joan's weekend mommy look here. If we had a friend who dressed like she did, we would want to spend everyday on a boat just looking super cute.

6
Joan Holloway
Joan Holloway
AMC

Season 7, 1969

Joan's more settled into herself now that some years have gone by; with her child at home and her growing importance in the office, looking relaxed and beautiful in this polka-dot number.

5
Joan Holloway
Joan Holloway
AMC

Season 7, 1969

Season 7 brought us a Joan that was powerful and sexy all at once -- just like we know she is.

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4
Megan Calvet
Megan Calvet
AMC

Season 4, 1964/1965

We first meet Megan when she's a receptionist at SCDP before she makes the rise to Don's secretary. While the color itself is familiar from what Megan typically wears, the tone down patterns makes this look seem mostly conservative for her.

3
Megan Draper
Megan Draper
AMC

Season 5, 1966/1967

Arguably the most iconic thing Megan has worn on the show thus far, Megan's sleeves made almost as much of an impact on viewers as her song and dance did.

2
Megan Draper
Megan Draper
AMC

Season 6, 1967/1968

Megan loves matching her salmon tones to gold and we have to say that we like it a lot too!

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Megan Draper
Megan Draper
AMC

Season 7, 1969

The longer Megan stays in California, it seems her hair just gets higher and her prints get funkier. And we like that just fine.

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