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Betty Draper or Jackie O? What a mom’s clothes say about her

U.S. first lady Michelle Obama

Charles Ommanney

For most women, the earliest exposure to fashion comes via Mom, the alpha and omega of feminine behaviour. We remember watching her dress, coveting her Pucci handbag. We recall shadowing her in the bathroom mirror, transfixed as she "put on her mouth." Some of us even took note of the lack of heels and how the hair grew grey and lovely.

So here's a parlour game (or something to go over with your therapist): Was your mom an icy Betty Draper or a blue-collar Roseanne Conner? Did she sport a cinched waist or an elastic one? A pillbox hat or mom jeans?

The real question driving the game is: Do a woman's clothes reflect how she mothers? And what does it mean to dress like a mom anyway? While pregnant, I wondered if I would have to trade in my wardrobe like I had had to trade in my body. Putting on those post-baby outfits was yet another marker of how much had changed: The old me didn't fit, literally or metaphorically. The first weeks and months of biological motherhood render style much less important than absorbency, as all material must be ready for the leaks and tears, the baby's and your own. I remember somewhere in that hazy first month looking down at my yoga pants and T-shirt soaked with breast milk and barf and thinking, "Everything is greige." The only colour I wore was purple – in the bags under my eyes.

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Of course, there's a tinge of pride in dressing like a haggard mom. Dishevelment is a badge of maternal selflessness, a sign that your priorities are elsewhere, with the child. Vanity is vanquished, but not being vain becomes its own kind of arrogance (what the Internet calls "the humblebrag"): The more tattered the T-shirt, the more serious the maternal devotion.

But surely benign fashion neglect is preferable to the obsessive perfection of the archetypal Bad Mom. This is Betty Draper's category. The crinolines under the skirt and the shellacked wave in the dyed hair of Mad Men's starchy matriarch are physically distancing – you can't wipe noses with white gloves. Bad Mom is dressed appropriately for a woman whose children are presented only occasionally, like a cheese plate, by a fleet of paid staffers doing the actual labour of parenting. Queen Victoria probably didn't hug those nine children not only because she believed that hugging was weak, but because it's very hard to bend at the waist in a bustle. The monstrous Joan Crawford – at least the version cemented by her estranged daughter's perspective in the tell-all Mommie Dearest – expressed her controlling personality in her tailoring, with her internal organs flattened by the stiff panels of suits and pencil skirts. There's a violence in that kind of sartorial containment that matches Crawford's alleged rages over her daughter's use of wire hangers.

But somewhere between Joan Crawford and Roseanne, Demi Moore stood naked and hugely pregnant on the cover of Vanity Fair and the look of motherhood was forever altered. We are now two decades into the age of the Yummy Mummy, a celebrity-magazine creation that has leaked into the real world. The phrase is evoked in workout routines, clothing lines and diets – all in service of the taut, mortality-busting skinny ideal that's really only attainable for those who can afford trainers and personal chefs. Not only are moms still struggling to find the chimeric work-life balance that eluded their own Second Wave mothers, they now have to add perfect wardrobes and a rock-hard core to the to-do list (also, please redecorate your living room and bake a retro apple pie – but don't eat it. Thank you.)

For most of us, the look of motherhood occupies a space between sweatpants and stilettos. In the early fifties, psychoanalyst Donald Winnicott described the "good-enough mother" as attached to her child but still independent and far from perfect – a healthy ideal of commitment and distance. Moms wondering who to emulate should perhaps take heed, abandoning hope of stylish perfection and looking toward "good-enough" fashion icons.

Begin, perhaps, with the enchanting Literary Mom. For me, these were writers of the seventies and eighties, the women my mother read and whose author photos I would study. There was Margaret Atwood, with loose curls, scarves around her neck and always the same Mona Lisa smile – serious bohemian chic. Joan Didion's early work always contained descriptions of her wearing a "shift" – such an evocative, solid word and garment. A woman in a shift has places to go. Didion completed her look with giant sunglasses, a cigarette and a purse big enough for a notebook.

It's possible that Literary Mom – a subspecies of Working Mom – may not get the biggest Mother's Day bouquet. Rebecca Walker still grumbles about Alice's parenting, but she did inherit her ability to layer necklaces. For all of these women, there were children, both in and out of their stories, but there was also a confidence in the way they dressed. They were mothers, but not just that.

Sharing a similar space with Literary Mom is Rock Mom. Patti Smith left her New York vagabond youth to move to Michigan for the carpool years, but she never strayed from her signature gaunt androgyny. The white shirt and skinny black tie that she wore on the cover of Horses, her hair slashed in a Keith Richards mass, is a timeless look, as defiant and in vogue now as it was in 1975.

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The mom who continues to rock provides assurance that the wild side does not vanish the moment one gives birth. Indeed, Gwen Stefani's coolest style incarnation – replacing the belly shirts with her current glam-punk uniform of drapey pants, high ankle boots and poppy-red lipstick – has coincided with motherhood.

While Rock Mom loudly claims her space, Public Mom makes both mothering and dressing look effortless Michelle Obama wears conservative, sleeveless dresses but in rainbow colours – a hint of the playful in the formidable (which may be another definition of the "good-enough mom"). It was wince-inducing when she reduced herself to "mom-in-chief" during the last election, but Obama is savvy: The mom card has political capital. It's a quick way to humanize powerful women as well as their husbands. Jacqueline Kennedy Onassis in an ivory-silk Oleg Cassini dress was even more loved when the outfit was accessorized with John Jr. pulling at her triple-strand pearls.

Though not yet achieving Jackie-level sophistication, Sophie Grégoire, wife of Justin Trudeau, might yet bring some style to Sussex Drive. A former model and Holt Renfrew buyer with a penchant for purple, she could be the most fashion-forward high-ranking political spouse since her mother-in-law (pantsuits!).

Ultimately, stylish moms serve as reminders that the expressive, joyful, creative parts of the self don't end when motherhood begins. I remember a veteran-mom friend visiting me during the overwhelming first days with my baby, saying: "Don't worry, you still have your brain." That was the most important – and comforting – truth. But it was also good news to discover, eventually, that I still had my closet, too.

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