After Sterling Cooper’s account executives devise an ad campaign that categorizes the female consumer as a Jackie or a Marilyn—the effortlessly chic first lady or the blonde seductress-actress—it’s clear that Betty Draper is a Jackie. And Clueless’ Cher Horowitz would say Jackie is actually a total Betty—timeless and fashionable. Regardless, Natalie Portman is in good company as a modern-day Ms. Draper; her frills-no fuss approach to clothes and adoration for uncomplicated details appear as if she has a presidential bevy of stylemakers at her disposal.
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Like Peggy Olson, Rachel McAdams does not easily fit into the Jackie-Marilyn dichotomy. She’s been everything from a very mean girl to the wife of a time traveler, and each time, and her ambition takes priority over sitting front row at Fashion Week or appearing on TMZ out on shopping escapades. Yet she always looks the part: A girl-next-door true to her own style, tasteful and simple.
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The men at Sterling Cooper immediately peg their slinky office manager as the siren entertainer but note “Marilyn is really a Joan—not the other way around.” Often likened to Miss Monroe with her blond coiff and buxom shape, Scarlett favors form-fitting clothes that flaunt her enviable figure, one that would render the account men atwitter with lust.
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Anne Hathaway rarely makes a sartorial misstep, relying on elegant, structured ensembles that have secured her continuing reign over countless Best Dressed rosters. Like Betty Draper, she sticks to classic shapes that are both regal and demure and is skilled at flattering her porcelain skin.
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Before Tom, there was Dawson and his creek, where Katie Holmes began her career as a precocious tomboy on the WB series. The series and her adolescent look are now gone, like Peggy’s youthful ponytail lopped off last season. These two don’t underestimate the transformative power of a good haircut. One snip is only the beginning for the former secretary.
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The female half of Brangelina is now a tamer version of the femme fatale she once was (do we need to mention the vial of Billy Bob’s blood?); her mysterious sexuality would have sent the whole of Sterling Cooper running faster than the Cuban Missile Crisis did at the end of Season Two. But Angie still prefers the minimalist black on the red carpet, consistently confident, seductive, and vampy.
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Sex-inspired edginess aside, Sarah Jessica Parker relishes in femininity, updating tried and true classics with her typical modern sleekness. With her tasteful fancies for ruffles, bows, and flowers, is it any wonder SJP was tapped for this?
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While some might say Peggy is dumpy, she’s not clueless; she just has much more important things that occupy her hours like hiding a secret child, getting her own office, and stifling her attraction to the married Pete. Jennifer Garner’s checklist doesn’t include slaving over the latest trends either. Uncomplicated and straightforward—who has time for anything else when you’re juggling a soaring career, two kids, and an equally successful husband? She knows that the basics are just as flattering as riskier choices, but you won’t be seeing her in high-waisted Mom jeans.
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Lucky lady: Salma Hayek’s husband, François-Henri Pinault, helms French luxury group, PPR SA, which operates, among other high-end companies, YSL and Balenciaga. As if her fierce physique didn’t inspire enough jealousy, now her closet is surely stacked (no pun intended) with a deluxe wardrobe that would spark some serious conflict among the secretary pool.
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Renée Zellweger opts for tailored ensembles that go perfectly with a strand of pearls and kitten heels. Don Draper may be no Mr. Darcy, but one glance at her graceful A-lines and refined accessories, and we forget Zellweger’s most famous alter ego is a slovenly singleton who prefers to chug vodka in her sweatpants over sipping martinis at the club.
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Peggy’s hard-earned entrance into the copywriting circle at the office leaves her more befuddled at how to handle the liquor-swilling and, yes, misogynistic antics of the men. Take a page from Sandra Bullock, who takes top billing with some of the finest leading men in Hollywood but manages a stealthy career, a sophisticated look, and brainy business choices. Result? Yowza.
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If Joan were around today, certainly her iPhone would be set to “Bootylicious”—Beyoncé’s hip-hop paean to the female figure. For the shapely singer’s 2009 world tour, she hired French couturier Thierry Mugler to up her provocative wardrobe, waist cinchers and hip padding amplifying her natural silhouette.
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