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Peggy Olson (Elisabeth Moss) goes through the most noticeable physical (and occupational) changes throughout the series. Starting out Season 1 as Don Draper's lowly new secretary, Peggy sports a mousy ponytail and outdated silhouettes. In spite of the naysayers (and there are a lot of them!) and a ridiculously secretive pregnancy, she manages to rise quickly in the ranks at the Sterling Cooper agency, first becoming a copywriter and is eventually promoted to the creative department at Sterling Cooper Draper Pryce. Peggy's style evolution reflects her personal growth as well as the changing times: Her pony gives way to a teased bouffant, her outfits start to actually match, and she even rocks the odd pillbox hat.
Joan Holloway Harris (Christina Hendricks), the femme fatale office manager at SCDP, has the most unchanging style of the lead characters in Mad Men. Her wardrobe seems to reflect that "If it ain't broke" mentality: Her clothes are always extremely sexy, fitted, and often constructed of wool or ponte, and
Sally Draper (Kiernan Shipka), the daughter of Don and Betty, has really started to come into her own. As her character gained importance in the second season, her changing style followed suit. Sally started out as a typical little kid with a seemingly awful mother-- how sad does she look in that nightgown! But by season 4, Sally had chopped off her hair and started wearing little shift dresses. And began seeing a therapist, because, clearly, people who cut their own hair are mentally unstable.