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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.

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.)

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.

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.

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.

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.
country polo shirts 'Mad Men' Character Has Come A Long Way PHOTOS