Peggy Olson's Style Evolution: 'Mad Men' Character Has Come A Long Way (PHOTOS)

Posted: Updated:

"Mad Men" Season 7 is coming, and we deserve it. (We work so hard, guys. We deserve a TV show about people who also work hard.)

With the show entering its final season, obviously everything about it needs to be analyzed. That’s why we’ve taken a look at Peggy Olson’s style evolution throughout the series so far. From A-line skirts and plaid pantsuits, we’ve documented our thoughts and feelings in hopes that somehow, "Mad Men" gets here before Sunday.

Story continues after slideshow:

Peggy Olson's Style Evolution
Share this
Current Slide

The meek Shall Inherit The Earth

"You’re in the city now," Pete Campbell tells Peggy at the start of Season 1. "It wouldn’t be a sin for us to see your legs." And that’s how we meet her: scared, unsure, and a far cry from the woman she develops into at the close of Season 6.

In fact, the majority of the pilot focuses on Peggy Olson from an aesthetic standpoint. On top of Pete telling her that if she pulled her waist in a bit she "might actually look like a woman" (honestly, die Pete), Joan tells her to go home, place a paper bag over her head, and really evaluate where her "strengths are." And Peggy has none of it. For the first half of Season 1, we see her in simple, modest styles. Girlfriend is about that corner office, and if men don’t have to object themselves to certain style codes, neither should she. Despite, of course, trying a little with that lovable neck scarf.


But thanks to Pete’s late-night house call at the end of the season’s first episode, Peggy Olson finds herself in a "delicate condition" – though neither her nor we are aware of it. She splits her skirt; Joan lectures her on eating "too much lunch," and the staffers at Sterling Cooper openly mock her about her increasing size. (Because they’re horrible.) But despite her unflattering skirts, jackets, and the opinions of her terrible co-workers, she still rises through the advertorial ranks. And by the end of Season 1, she’s a junior copywriter – and a woman in labour.

Check And Mate

The next time we see Peggy, she’s home from the hospital, she’s back to her small size, and she’s wearing a fitted late ‘50s/early ‘60s dress that Joan eventually likens to that of a little girl. In fact, this is how Peggy dresses until mid-to-late season, when she cuts off her hair, and grows into maturity so impressive that she tells Pete about their secret love child and walks out of the office with the coolest nonchalance of all. (Even better because he’d just confessed his undying love for her. Later, Pete.)

They Keep Getting Older, She Stays The Same Age

But while Peggy’s obviously grown from her secretarial roots, she’s still not the force at Sterling Cooper that she goes on to be. She shares an office with the copy machine, she’s still treated like an assistant, and her wardrobe reflects it: she may be Peggy Olson who wants to smoke some marijuana, but she’s doing it in a plaid skirt and blouse with a bow. Unlike Season 4.

"The Suitcase"

Behold: the last time we see Peggy wearing something so obviously associated with her former self. In perhaps one of the greatest episodes of any show ever ("The Suitcase"), Peggy stays at work despite it being her birthday – then finds herself in the midst of a Don Draper meltdown, where she’s ultimately (finally) acknowledged as his equal. However, what’s most interesting (seriously, let’s talk about this) is her literal shedding of the past: after taking her hat off (a very Peggy Olson-in-Season-2 choice, let’s add), we never really see it again (when Don’s throwing up, she’s even holding his hat). And from there, her style really develops.

Joyce And Co.

This is also the season in which Peggy meets Joyce (mother of "Girls'" Shoshanna, let’s pretend). And with Joyce comes entry into a much hipper, younger world than the one Peggy’s previously been in. We see Peggy in a turtleneck, for heaven’s sake (at an art show). Her blouses may still have bows, but they’re more streamlined; more businesslike – more something you’d see Dolly Parton wear in "9 to 5." These are career clothes a.k.a. the official Olson uniform.


Which brings us so one of the most powerful moments in Peggy’s storyline: after years spent calling out sexists (see: Joey and his drawing of Joan), working in the nude to call Stan’s bluff (although, yes, that was only one time) and finally being poached by a competitor’s agency, she leaves Don Draper and Sterling Cooper behind, all while wearing a simple purple dress that’s neither over-the-top or boring. It’s classic, and it’s Peggy. After all, the loudest one in the room is the weakest one in the room – and there’s nothing weak about Peggy at all.

Making It Rain

And so we enter into Season 6, in which Peggy Olson is on a Don Draper level of success. She’s got her own office, her own interns, and a boyfriend who, frankly, doesn’t get her/it. (Whom she dresses down for, let the record state.) But Season 6 sees Peggy’s last installment of "safe" clothes: after reuniting with Don and friends, she’s still all business, but more on-trend. (Especially as evidenced by her formalwear.) This is a Peggy that takes risks because she can, and shells out for new clothes because her paycheque allows it. But just when you think she can’t throw any more curveballs, boom.

Better Off Ted

And then Peggy falls for Ted. And in an attempt to earn his attention back (honestly, this man was a garbage person), she leaves work one day in a dress no one every thought we’d see her in: little, black, plunging, and containing pink. Which works! Briefly, that is, before Ted shames her and says the affair can’t continue (because, as established, he’s a garbage person). While that conversation happens, we see Peggy in a low-cut (rare) dress with a call-back to Season 1 (unrequited love, volume 1) with her neck scarf, and the next time we see her, everything’s changed.

Corner Office Realness

So take that, Ted: Peggy’s got the other corner office. And to further establish the miles travelled between Season 1 and Season 6, Peggy sits down in said corner office (in Don Draper’s chair) wearing a plaid pantsuit – the boldest look she’s embraced that’s had nothing to do with men. Maybe you pull your waist in, Pete. Peggy’s your boss now.

Around the Web

Peggy Olson - Wikipedia, the free encyclopedia

Mad Men - Peggy Olson – AMC

Peggy Olson (PeggyOlson) on Twitter

Moss: I'll keep Peggy Olson's ring

Mad Men's Janie Bryant on Subliminal Messages, Peggy's Rise

'Mad Men' Where They Were: Joan Harris

'Mad Men': TV review

10 Crazy Things You Didn't Know About The Hair On "Mad Men"

Don Draper 1925 – 2001: An ad man for all seasons

My Course on Mad Men Taught My Students How to Be Smarter TV Watchers. It ...