Editor's note: Rachel Weingarten is a style expert and brand consultant. She teaches beauty history and marketing at the Fashion Institute for Technology and New York University and is the author of "Hello Gorgeous! Beauty Products in America '40s-'60s." Find her on Twitter @rachelcw
(CNN) -- Two iconic women with seemingly radically different world views died recently, leaving legacies of humor, pioneering spirit, and striking public personas.
As divergent as their styles were, former Cosmopolitan editor Helen Gurley Brown and comedian Phyllis Diller each used their appearance as a means to an end: Diller to make herself the butt of the joke, Gurley Brown to get ahead personally and professionally -- and to show generations of women how to do the same. Whether chasing beauty or mocking it, these women broke ground by reflecting and reshaping the values of their eras while paving the way for the women behind them.
Original mad women
Like Peggy Olson in the AMC TV series "Mad Men," at midcentury Diller and Gurley Brown both worked as advertising copywriters early in their careers. They each segued into more recognizable versions of themselves as they approached their 40s, carefully crafting their looks and personas into brands that would become instantly recognizable to the American public. Both women would display a penchant for plastic surgery and outlandish style, using themselves as canvases to depict the life of the modern woman.
A girly Gurley
In an era when settling into marriage and family young was the norm, Gurley Brown married at 37 and took over the helm of Cosmopolitan magazine at 43, a position she held for more than three decades. Her 1962 book "Sex and the Single Girl," was the precursor to "Sex and the City." It was also the hopeful embodiment of the "fun, fearless female" ethos later instilled in hopeful Cosmo girls everywhere.
In reality, Gurley Brown, who died last week at 90, gave up the single life to become the devoted wife to husband David Brown until his death in 2010. (A New York Times obituary quotes her as saying, "I looked after him like a geisha girl.") But she never gave up her fun, flirty, single-girl attitude.
Throughout it all, she exhibited a carefully lacquered persona, almost painfully thin, perfectly coiffed and manicured, with the occasional nip and tuck to retain her trademark waif-like look.
At the age of 37, Phyllis Diller was a harried homemaker and mother of five, who followed her husband's advice to try her hand at humor writing and performing. Unlike the perfectly polished TV counterparts of her era, such as Harriet Nelson or June Cleaver, Diller presented a more realistic version of marriage and motherhood that had more in common with "The Munsters" than "I Love Lucy."
And people loved it. Diller, who passed away Monday at 95, chose not to represent a prettified version of her life, but rather the outrageous extremes of family. Fictionalized versions of family members in her act included husband Fang, mother-in-law Moby Dick and sister-in-law Captain Bligh.
Diller's exaggerated makeup and wigs and outlandish costumes deliberately disguised her plain, if not beautiful face and womanly curves. In a 2006 interview in TV Guide, Diller talks about posing for Playboy magazine. As the legend goes, the editors hoped her appearance would be played for laughs but were disappointed to discover that instead of being bony and unattractive, she was simply shaped like a woman.
In a previous incarnation, I worked as a celebrity makeup artist and, among other things, worked with various Cosmo cover girls. They all seemed impossibly tall, aloof and preternaturally beautiful. I remember blushing to the roots of my hair at my first shoot after being singled out by Gurley Brown, who complimented my beautiful skin.
In 2006, I was called out of cosmetic retirement to do the makeup for the cover of a now-defunct literary magazine celebrating female writers and editors. I was delighted to see Gurley Brown, clad in her signature fire engine red suit and fishnets.
At 84, she was frailer than I remembered, but still sizzling. I reminded her of our previous interactions and she looked at me and said, "That's well and good, and you still look pretty, but what have you done since then?" I was struck by the fact that a woman who had built an empire atop the cult of female perfection didn't think that looking pretty was enough.
Pretty powerful pioneers
Both Helen Gurley Brown and Phyllis Diller created idealized versions of themselves to sell their products. Both were groundbreaking thinkers, businesswomen and performers. In one way or another, both used their faces and bodies as their calling cards.
Gurley Brown paved the way for women like Jane Pratt to create careers and publications that celebrated the multi-faceted modern woman. She also made room for magazines including Bust and Bitch or websites like Jezebel that thumb their nose at everything she'd worked for and stood for.
Diller opened the door for comedians like Carol Burnett to ridicule the classic feminine ideal (see Burnett's riotous Scarlett O'Hara bit), and for Roseanne Barr to lead a sitcom as the anti-mom in looks, shape and demeanor.
More than that, she led the way for traditionally feminine-looking, yet frequently foul-mouthed comedians including Sarah Silverman and Chelsea Handler to be outrageous while remaining attractive.
Gurley Brown and Diller were tough and successful and lived life by their own rules. They were two sides of a coin that paid the dues for women in today's media landscape.
Share your favorite memories of Helen Gurley Brown and Phyllis Diller in the comments section below.