‘Toddler Grandma Style,’ The Fashion Approach That Will Set You Free

By Cynara Geissler

Dress for the second-birthday/retirement party you want your life to be.

Ever heard Jenny Joseph’s poem that begins “When I am an old woman I shall wear purple / with a red hat which doesn’t go, and doesn’t suit me,” and dreamed of being one of those devil-may-care old ladies? Or listened to an expecting friend talk enthusiastically about how fun it is to shop for baby clothes — the prints! The colors! The animal-hooded onesies that are basically the comfy Halloween costumes of your dreams! — and wished that you could have that much fun with clothes? Here’s the thing: You don’t need to wait until you can join a Red Hat Society and/or acquire small children to escape the tyranny of normcore. You can have it all — the fun, the pizzazz, the animal hoodies, the lack of fucks to give about whether your Agent Carter-inspired hat looks good — right now.

We all have internalized ideas about what it means to “dress like a grown-up.” (A leather briefcase full of bills stamped “PAID” is one of the things I picture, for example.) But these ideas tend to have a common theme, and that theme is tidy, quiet, and contained. For almost a decade, What Not to Wear’s Clinton Kelly and Stacy London put every single woman who appeared on their program in the same bootcut dark denim, black blazer, and straight, blunt bob haircut in the name of “professionalism.” Our culture has absorbed and perpetuated the mind-numbingly dull idea that the best way to signal that you are a smart adult woman is to don suit jackets, favor neutrals, and wear heels.

Our culture has absorbed the idea that wearing neutrals is the best way to signal you’re an adult.

I’d like to pitch you a different approach, an approach that also happens to be the guiding principle of my wardrobe: Toddler Grandma Style.

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I first heard the phrase “toddler grandmother” on an episode of the Fox series Glee in 2009. The diva high schooler Rachel (played by Lea Michele) is described as dressing “like a toddler and a grandmother at the same time.” What that means is Rachel wears flats and Mary Janes, tights and knee socks, pastel harlequin-print polyester dresses with Peter Pan collars, button-up cardigans, headbands. It’s meant as a huge diss, a slam on Rachel’s inability to sexy herself up properly — toddlers and grandmas are about as sexless as you can get, and the combination is a big, transgressive yiiiiikes. Of course, this episode ends with Rachel getting an Olivia-Newton-John-at-the-end-of-Grease-style makeover. (Really though, when a makeover involves subtracting personal style instead of adding any, it’s actually a make-under.)

The message of the episode was clear. Even “divas” (an Italian noun for female deity), who by definition should get to be incredibly loud and larger than life, are expected to contort themselves to fit a narrow standard of beauty with ever-moving goalposts: Turn it out just enough that men notice you, but also, dial it back so you don’t call too much attention to yourself and intimidate men.

2009 is also the year that Leandra Medine founded her counter-cultural style blog Man Repeller. Here’s part of the manifesto:

“A Man-Repeller is she who outfits herself in a sartorially offensive mode that may result in repelling members of the opposite sex. Such garments include but are not limited to harem pants, boyfriend jeans, overalls, full length jumpsuits, jewelry that resembles violent weaponry and clogs.”

The title of the blog itself points to a dominant cultural assumption. Women dress (or are expected to dress) in a way that should attract the straight male gaze. Leandra, with her predilection for drop-crotch lime green utility pants, a top knot, and an “arm party” full of bangles, is playfully and actively resisting the idea that style should be about pleasing some man first (as opposed to pleasing yourself).

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For me, these two cultural moments matched as beautifully as saddle shoes and ruffled ankle socks. Toddler Grandma Style was my chance to embrace all the noisy novelty prints, sensible shoes, and Claudia Kishi accessories (excessories) I loved, while also living the patriarchy-flouting, male-gaze-dodging ideals of a Man Repeller. Because toddlers and elderly women are seen as devoid of any sex appeal, they stand outside the male gaze and as such get to ignore the rather limiting “rules” set out for women (in culture, and by ourselves) when it comes to personal presentation. Nobody would ever suggest that you outfit a baby in head-to-toe tailored neutrals, or that a tutu on a 3-year-old is inappropriate outside of a dance studio. Similarly, you would never suggest a silver-haired septuagenarian was unprofessional or “underdressed” if she’s not wearing impractical toe hammering stiletto heels.

Why should whimsy and comfort only be available to women under 5 and over 65? Why are we supposed to prove we are serious, smart, and professional by dressing in a color most commonly used to paint luxury condos (“Yaletown greige”)? Because we’re supposed to make ourselves the right kind of fancy (or invisible) for men? Well, fuck men. If anything, our wardrobe options should increase when diapers are no longer (and not yet) a wardrobe staple.

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As a 33-year-old woman with a professional job, I reject the idea that I have to dress like Melanie Griffith in Working Girl to TCB. We only suffer, aesthetically and physically, when we judge a woman’s ambition and abilities by the precariousness of her heels and density of her shoulder pads.

Of course, we cannot avoid sending a message with our clothes or being read by the people who see us out in the world wearing them. “Grooming practices,” writes Jennifer Scott in Fresh Lipstick: Redressing Fashion and Feminism, “mark a society’s members by rank, gender, occupation, and age, and also communicate identity, affinity, or aspiration. Failure or refusal to groom communicates resistance, carelessness, or incapacity. No one can dress in a way that signifies nothing.” Toddler Grandma Style, like any style, does have a message. The message is “boys, this isn’t about you.”

Toddler Grandma Style has a message: Boys, this isn’t about you.

I get told pretty often “I could never wear that, but you, can pull it off” — as if I’ve got some VIP pass that other women don’t. The thing is, in many ways, I am the furthest thing from designer’s minds. I don’t have a model or “clothes rack” body; if the contestants on Project Runway were tasked to make a dress for me, they would probably all throw themselves under an actual bus. I am not tall, and I am not thin. I have a “weird’ haircut that I often style like a cream horn. In fact, maybe that’s why people think I can “pull it off” — because I already fall so far outside the narrow norms of beauty that I can just throw my hands up and do whatever I want. (That, and I have serious skepticism for clothing rules and a total lack of impulse control whenever I see a dress on Modcloth that is printed with any type of cat.)

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They’re right that being fat gives me an edge here, but that’s not why. It’s because there is an actual real secret to developing personal style, and it is not in fact a secret if you are fat and born before 1980 and wanted your clothing to look somewhat “contemporary” (never mind chic). Before these glory days of extended sizes at Forever21 and H&M, fat people who weren’t satisfied by the basic offerings of the few plus-size chains were forced to lifehack the shit out of thrift stores and department stores, ignoring size labels and risking dirty looks from sales people to find anything sexy or cute or remotely interesting. What we learned: sizing is wildly inconsistent. Jersey fabric is magical. Oversized pieces on one body can be sleek and sophisticated pieces on another, and neither of those is the “wrong” way to wear it.

But most importantly: you will really have no idea what will fit you and actually look good on you (I mean physically on your body but also spiritually in your soul) until you take time to TRY SO MANY THINGS ON. Armloads of things. In the fitting room for over an hour amounts of things. Things you are drawn to despite ideas about what colors or cuts or fabrics someone with your particular collection of traits is supposed to be “allowed” to wear, according to some magazine or lifestyle program that’s never had your best interests at heart. There will be a lot of misses, and you’ll learn that the misses don’t matter. What matters is getting outside of your comfort zone.

When you try on a lot of clothes, your perspective shifts. You become open to possibility.

Cast your mind back to 2001, or thereabouts, when the idea of wearing anything other than a flared or wide-legged jean was unthinkable. Any other cut of denim, especially tapered, looked odd or felt dated. Then runways began to feature slim suit pants and skinny jeans and these options became available in high street stores — and the more we saw them, the more normal and then the more attractive they unconsciously became. We all experience the widening and shifting of our aesthetic eye every time a trend like slim denim or high-low hems takes hold of the public fashion imagination: what once looked transgressive or wrong feels fresh or inspiring. The very same thing can (and does) happen on a personal scale when you deliberately try on a lot of different clothes and really think about what pleases you. Your perspective shifts. You become open to possibility.

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Starting right now I’d like to invite you embrace any/all of the following tenets of Toddler Grandma Style that speak to the toddler you once were and grandma you could become:

  • You can wear as many layers as you want; you don’t have to worry about “adding bulk” or be expected to “show off your shape.”
  • You are not limited to only one bright color at a time.
  • Patterned or neon tights >>> “flesh-colored” tights that are probably someone else’s flesh color anyway.
  • Overall jorts are actually good.
  • You’re allowed to mix multiple prints (floral, plaid, big stripes, ditsy prints, cat prints) in the same outfit.
  • Plaid pleated skirts are not just for private school students anymore!
  • Sailor-themed frocks: SET SAIL FOR SARTORIAL ADVENTURE.
  • Midi- and maxi-length hemlines are not just for tall girls.
  • Don’t worry about pairing sneakers or chunky shoes with dresses.
  • Go ahead and wear large, non-delicate costume jewelry.
  • Wear bows in your hair! On special occasions you can even level up with real hummingbirds for extra VOLUME.
  • Purses shaped like animals or fruit are probably the best purses. (I have an apple-shaped purse I often put an apple in. That bit never gets old to me, or to anyone who witnesses me take an apple out of that purse).
  • You can wear brooches! You can wear MORE THAN ONE AT A TIME!
  • Short haircuts look good on EVERYONE, and even if they don’t who cares.

Some of these will make you feel good, and some won’t, but you won’t know until you try. Why not dress for the second-birthday/retirement party you want your life to be? You have nothing to lose but your self-imposed wardrobe restrictions.

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