What the Baby-Sitters Club Wore (And What It Meant)

What the Baby-Sitters Club Wore (And What It Meant)

There’s something about the outfits in the Baby-Sitters Club. And it’s not just Claudia’s decadent concoctions. The members of the BSC use clothes as armor, as costume, as adolescent exploration of self in a way that still feels very real thirty years later. The club’s style choices stuck with us—ask any millennial bookworm to describe the babysitters, and you’ll probably get a pretty complete sartorial picture, from their baseball caps (Kristy) to their wire- rimmed glasses (Mallory) to their double-pierced ears (Dawn). When I first revisited the series in the mid-aughts, I was a wayward twentysomething browsing thrift store bookshelves. Every book I opened felt like coming home, and the outfit descriptions were especially familiar. Which makes sense, considering the amount of time I’d spent poring over them as a child. Those outfits unleashed an incredibly strong sense of nostalgia, maybe even more so than the plots. Reading a good outfit description put me right back in my childhood bedroom, imagining how cool the babysitters must’ve looked in their high-top sneakers.

I wanted to share that feeling of side-ponytail-induced time travel, so I started a blog to catalog the outfits of the most iconic dresser of the series, Claudia Kishi. Claudia’s style is so bombastic and maximalist that an outfit description could easily take up half a page. While What Claudia Wore’s original focus was limited to the zany creations of the club’s vice president, it soon grew to include the rest of the club. As it turns out, fashion served the sitters in a multitude of ways. Style lessons and fashion journeys were as much of a constant in the books as babysitting adventures.

Kristy Thomas Invents the Concept of Uniform Dressing

And we didn’t even appreciate her innovation. While a personal-style uniform is now widely accepted (think Elizabeth Warren’s jewel-toned cardigans and blazers over black shirts and pants, Emmanuelle Alt’s luxe tops belted into impeccably tailored pants, or Ariana Grande’s oversized sweatshirts and thigh- high boots), Kristy’s choice to embrace wardrobe monotony is bemoaned by both readers and her fellow babysitters. All those chapter 2 outfit descriptions— when the narrator even bothered to walk you through Kristy’s outfit—were pretty much the same: that time-tested combination of a turtleneck, jeans, running shoes, and maybe a baseball cap. As a character trait, it’s shorthand for Kristy’s pragmatism and tomboy nature. And sometimes, in less generous retellings, her immaturity. We delighted in the paragraph-long walkthroughs of Claudia and Stacey’s style creations, and our eyes glazed over reading yet another Kristy sweater-and-jeans combo.

But today, with the concept of uniform dressing heralded as smart, mini- malist, and effective, we can look at Kristy’s closet with a new eye. Advocates of the personal style uniform (from entrepreneurs like Richard Branson to min- imalist writers like Joshua Becker) point to it as a productivity enhancer, and who is more productive than Kristin Amanda Thomas? Concepting businesses (the BSC), products (Kid Kits), and line extensions (mini-camp). Undergoing a long daily commute (from the upper class neighborhood to Stoneybrook Middle School via bus, while her friends have the luxury of walking or bik- ing). Even, for a short while, running for public office (eighth grade president) before recognizing her bandwidth limitations and stepping back. Adherents to uniform dressing say it reduces decision fatigue. As CEO of the BSC, Kristy is certainly more susceptible to decision fatigue than your average eighth grader. How’s she gonna have time for all those great ideas if she’s distracted by a closet full of options?

Claudia Kishi Is Her Own Best Canvas

For vice president Claudia Kishi, a closet full of options isn’t just fashion, it’s freedom. For someone who feels like an outsider within her own family, getting dressed is as much an act of rebellion as it is self-expression. Claudia is a character of contradictions: at once one of the coolest girls in Stoneybrook Middle School, and also an outcast who’s never had a best friend until stylish Stacey McGill moves to town. She’s a dedicated artist who is devoted to hon- ing her craft, and also an absentminded student who can barely bring herself to pay attention in class. She’s so grandly experimental with clothes that she’d likely be ostracized for it in most middle school settings, but her absolute joy in getting dressed makes her able to pull off anything, as her fellow club members assure us. Even bungee-cord belts.

Claudia’s outfits are bold and celebratory, showcasing her artistic spirit. But there are times when they backfire, activating her insecurity about her place in a conservative family of bankers and librarians. It happens in book #33, Claudia and the Great Search, when Claudia attends an academic award ceremony for her genius sister, Janine.

“Janine was wearing one of her usual plain outfits,” she narrates, “a long pleated plaid skirt, a white shirt with a round collar, stockings, and blue heels . . . I on the other hand was dressed in one of my usual wild outfits—a very short black skirt, an oversized white shirt with bright pink and turquoise poodles printed on it, flat turquoise shoes with ankle straps, and a ton of jewelry, including dangly poodle earrings. . . . People kept looking at Janine and then looking at me. I could just tell they were all thinking, I can’t believe you’re sisters. Then they would ignore me and congratulate Janine. I could not wait to leave that auditorium.”

Now, probably most of us would feel a little self-conscious in a poodle-print shirt and matching canine earrings. But this is an aberration for Claudia, who typically takes her family’s bemusement in stride, brushing off comments like “interesting outfit, honey” with a breezy “thanks!” Because Claudia doesn’t dress for the outside world. When she’s lying in bed concocting her next com- plicated outfit, she’s not doing it for adolescent approval or to catch the eye of a boy she likes. It’s a way to turn her body into her own canvas, an eternally morphing art project. And with the next day’s masterpiece identified, she can reach under her mattress for one final Mounds bar and drift off into peaceful, self-actualized sleep.

The Slow Style Evolution of Mary Anne Spier

If Claudia’s style is the most memorable, club secretary Mary Anne Spier’s might be the most controversial. Her transformation starts with letting her hair down (literally) in book #4 and culminates in the friendship-disrupting short haircut and floral-print leggings of #60, Mary Anne’s Makeover. While her new look isn’t scandalous in and of itself, it triggers a lot of insecurity and hurt feelings. Mary Anne is seen as so reliable and predictable that the minor surprise of a mall makeover sends shock waves through the club. Who knew a little eyeliner could be such a crime?

Mary Anne’s slow coming into herself makes sense for the shyest, most sensitive member of the club. Her family is small, hobbled by the trauma of her mom’s death. In her first book of the series, she tells us that her uptight, conservative father asks God to watch over her mother at every meal. It’s a heavy weight to live under, especially as an only child. And Richard is a clue- less father, dictating a little girl room (she still has a framed image of Humpty Dumpty on her wall at age twelve) and a school-uniform style of dress, all pleated skirts and braids and Peter Pan collars.

It’s her adventures in babysitting that inspire the courage to change. After a harrowing trip to the emergency room with a four-year-old running a 104 degree fever, Mary Anne’s dad realizes she’s growing up. And after her ordeal, not to mention a nearly club-ending fight, Mary Anne has the courage to remind him that she’s almost a teenager now. She gets permission to update her room, to relax her style a little bit, and even to baby-sit until 10 pm on Fridays and Saturdays. She’s still conflict-averse, quick to cry, and more comfortable within a crowd than in front of it. But throughout the series, she learns to stand up for herself and listen to her own instincts more than the opinions of others.

And then comes that makeover. Inspired by a model in a magazine, Mary Anne decides to get a super short haircut. Stuffy Richard even takes her to the mall to get it. Everyone at school is surprised but complimentary about Mary Anne’s transformation (despite the fact that, as most of the book covers depict, it is basically a mushroom cap of hair) except her best friends. Middle school ostracization is a norm, of course, but it’s shocking for it to happen between this set of friends. The Baby-sitters Club is so wholesome, so pure in their love and support of each other, that real moments of strife between members are series-defining events (Ann M. Martin upped the ante in #100 with the high drama of a temporary club disbandment). And it’s almost as painful for the reader as it is for gentle Mary Anne to see her best friends turn their backs on her. They come back together in the end, though, because of course they do. But it’s not the only time fashion becomes a point of friction between the club members.

Read more like this: Rachael Leigh Cook and Malia Baker on playing Mary-Anne in The Baby-Sitters Club decades apart

Stacey McGill Is More Chic Than You

Ask anyone to describe club treasurer Stacey McGill and they’ll say the same thing: she’s sophisticated. She’s from New York City. And maybe, if she’s passed them notes in the halls of Stoneybrook Middle School, they’ll add that she dots her i’s with hearts. Stacey’s city girl cool is her most defining quality. It’s consistently showcased in the way Martin and the ghostwriters dress her and position her against the rest of the club members. She starts off the series a little more wild and wacky (early books mention items like fingerless gloves and sparkly dinosaur pins on her beret) but settles into chic and sophisticated over time. It’s the late 1980s and ’90s, remember, and so this is signified with blazers, luxe fabrics, wool slacks, the color turquoise.

These big city vibes follow her to her new life in suburban Connecticut. Her mom works as a fashion buyer. Her dad maintains an apartment in the city where her sophistication education can continue. She’s totally at home in Bloomingdale’s. While she deeply appreciates her friendships with her fellow babysitters, it’s this cosmopolitan cool that can create rifts between them. We see this in #18, Stacey’s Mistake, when Stacey invites the club to New York City for a weekend. From the second they get off the train, Stacey finds herself feeling self-conscious about their visit—among other faux pas, Kristy is wear- ing a baseball cap with a border collie on it, and Mary Anne has her nose in a giant map of the city before accidentally shoplifting from the Bloomingdale’s makeup counter.

The worst fashion crimes occur at a party Stacey planned to introduce her small-town friends to her big-city ones. Despite her attempts to manage their looks, Kristy wears a white turtleneck with a red and blue heart print and Mary Anne “looked like she’d walked right out of the pages of Little House on the Prairie” in a ruffly white blouse, a long paisley skirt, and little brown boots. While Stacey eventually gets over her humiliation and the club relaxes into their visit (enough for Stacey to even invite them back for a longer stay in Super Special #6, New York, New York!), the feeling that she’s a little bit elevated from them never really goes away, and Stacey’s style serves as a constant reminder of it.

Dawn Schafer and the Legacy of California Casual

Close your eyes and picture another Stoneybrook transplant, West Coast native and BSC alternate officer Dawn Schafer. Cornsilk blonde hair, loose-fitting clothes . . . Dawn Schafer had a generally undone (but not sloppy) aesthetic that Ann M. Martin called “California Casual.” This turn of phrase came to represent Dawn as a whole—Dawn the ecologist, Dawn the vegetarian in a world of meat-eaters, Dawn the individual who got her ears double-pierced and wore earrings shaped like oranges to pay tribute to her home state.

Now picture Dawn today. She’s pretty easy to translate to modern times. She might be a Madewell model, the brand that defines itself by its tomgirl vibes and affinity for denim-on-denim. She might be a VSCO girl, in her oversized T-shirts and beachy accessories (puka-shell necklaces and Pura Vida bracelets could be the modernized version of orange-shaped earrings, right?), toting a reusable water bottle as an outward-facing sign of her low-waste life- style. You can easily place Dawn in 2020 not because of the specifics of her wardrobe but because of what it represented. Dawn is the cool girl. Not the trendy girl, like Claudia and Stacey, but the self-assured girl, the one who is always herself. She’s an individual without relying on flashy statement pieces to communicate this.

This is reinforced in #50, Dawn’s Big Date . . . aka the makeover that failed. Feeling insecure at the prospect of meeting Logan’s cousin Lewis, she’s convinced she needs a new image. Heavily applied navy blue eyeliner, hot pink lipstick, hair gel, black textured stockings and a rolled-up skirt—it just might be Dawn’s take on 1985s Desperately Seeking Susan. The look, along with the teen magazine flirting tips she tries out, lands with a splat. In the end, Dawn and Lewis agree to reintroduce themselves, which Dawn does sans hair gel, in faded blue jeans and a UCLA sweatshirt. (She also makes him a tabouli salad, ’cause if Dawn’s gonna Dawn she’s gonna Dawn all the way.) Ultimately, the lesson here is similar to the one Mallory learns in Super Special #5, California Girls: authenticity matters.

Mallory Pike and the Intoxicating Promise of a Makeover

Junior officer Mallory Pike was always the babysitter most susceptible to the power and promise of a makeover. As one of the two youngest members of the club, she’s often comparing herself to the endlessly glam Claudia and Stacey, or cool-girl prototype Dawn. Looking back to my own thirteen-year-old self, I have to imagine at least some of these girls were still in their awkward stages. But to Mallory, they were goddesses. Thank God she wasn’t acquainted with the Wakefield twins.

Mallory wore glasses. She had braces. Her hair was reddish-brown and curly, in an era before the Curly Girl Method helped women embrace their ringlets. As the oldest kid in an eight-child family, she was in the unenviable position of most mature, while still not being mature enough—for pierced ears, for cool clothes, for contacts. And when she finally gets to be a member of what she sees as the cool kids (imagine your dorky eleven-year-old self accepted by a group of girls two years older and seemingly the best of friends?), they put her through her paces to prove herself. For Mallory, even after club initiation ends, every club meeting serves as a reminder of her inferior looks.

Mallory’s second book, #21, Mallory & the Trouble with Twins, is a treasure trove of makeover fantasizing and realization—not just for Mallory but also for the titular twins, Marilyn and Carolyn Braddock, who are unhappy with their matching outfits and lack of recognition as individuals, and therefore need to go to the mall. A late ’80s fantasy shopping montage ensues, complete with a moon-and-stars sweatshirt, a pink denim skirt, headbands, and yellow push- down socks. The twins’ journey to self-expression inspires Mallory, who convinces her parents to let her get a haircut and pierced ears. It’s a grown-up mile- stone to Mallory, as it probably was to many of us—getting her ears pierced means having more in common with her eighth grade heroes.

Things don’t go as well the second time Mallory attempts an image make- over, during a club trip to California. (Superfluous to the makeover, reminder that this trip was funded by the Connecticut State Lottery because these girls are nothing if not lucky.) Inspired by a trip to the Max Factor museum and images of sun-kissed California girls, Mallory blows all her trip money on expensive makeup and blonde hair dye. (“Oh my lord,” is all Claudia can say post-blonde transformation.) It’s only after a casting director tells her that her looks aren’t quite right that Mal comes back to her senses, and when Kristy tells her she’s “trying to look like someone she isn’t,” Mallory finally snaps out of her California dreams. The club is supportive in her retransformation, help- ing her pick out a shade of red dye that looks closest to her natural color and celebrating the return of the Mallory they know and love.

Now, the image of an eleven-year-old with a blonde dye job and stage makeup is patently ridiculous, or at least it was in a pre-Kardashian era. Would Mallory’s blonde experiment have petered out on its own without the club’s disapproval? Most likely. But here the club’s resistance to change comes from love, not fear. When Mary Anne changed her style, it shook her friends’ sense of who she was and what their friendship meant (until they realized that nothing had changed besides ten or so inches of hair). But Mallory’s California makeover is the manifestation of all her adolescent insecurity, and here the club lovingly helps her regain her true self—curly red hair and all.

Jessi Ramsey Teaches Us to Dress for the Job We Want

Junior officer Jessi Ramsey has the least explored personal style of all the club members. Jessi’s identity revolves around her love for ballet, and that love tends to drive most of her plotlines. She’s more than just a dancer, of course, but in comparison to the rest of the club members she—and her relationship to clothes—seems underdeveloped. As millennials grew up from these books and gained a more mature lens, it has become clear to us how clunky (if well-intentioned) the series’ handling of race was. Giving Jessi a makeover journey or style evolution wouldn’t solve for that—but its absence, when it’s key to so many other stories of self-expression within the series, is worth noting.

And so, Jessi’s fashion story is entwined with her identity as a dancer. Book #16, Jessi’s Secret Language, begins with Jessi waking up at 5:29, before her alarm can ring a minute later. Immediately, we get it—she is an extraordinarily disciplined eleven-year-old, foregoing sleep to dress in her leotard and warm-up clothes and practice ballet in her makeshift basement studio. Jessi is the BSC’s embodiment of the fashion (slash professional) rule dress for the job you want. Like Kristy, Jessi is dressing for the future. She showcases her passion in her outfits—keeping her hair in severe ballerina buns, wearing leotards as shirts. She’s often running to babysitting jobs or club meetings from dance classes, and so this is a pragmatic decision as much as it is a style one.

But it also serves as a constant reminder to Jessi (and everyone around her) of where her priorities are. She is a dancer, she wants to be a professional dancer, and she carries that with her in dress as much as in her proper posture or natural turnout. You have to imagine that a kid so focused and disciplined at age eleven would end up going places.

It’s always fun to imagine what might have become of these beloved childhood characters as they grew up. Would Stacey, with her head for numbers and enduring love for the Big Apple, wind up on Wall Street? Would Claudia’s penchant for pattern-mixing make her the free-spirited darling of a Project Runway season? Would Dawn open her own co-op? (Yes, and the employee aprons are recycled lightwash denim.) But the enduring magic of this series is partly due to the way it freezes time for us—and for the sitters, who had endless eighth grade winter vacations and spring breaks—while showcasing its passing at the same time. I’ve gone from a seven-year-old reading about the coolest group of best friends I could ever look up to, to a thirty-something who now feels downright maternal toward these kids. What a journey, even if I never managed to pull off those double-layer slouch socks.

While the outfits themselves might be dated (though certain elements have come back around again thanks to the cyclical nature of fashion), the lessons are timeless. Growth and change are part of life, but authenticity is way more important than looking cool. Normal middle school jealousies arise but are always resolved, because ultimately the bond the babysitters share is bigger than any fashion differences or makeover misfires. In the end, everyone winds up back in Claudia’s room, laughing and sharing stories and pillowcase snacks—whether they’re wearing ballet flats or sweatpants. Where else could you possibly want to be on a Monday, Wednesday, or Friday at 5:30?

Excerpted from We Are the Baby-Sitters Club, edited by Marisa Crawford and Megan Milks, courtesy of Chicago Review Press. Essay copyright © 2021 by Kim Hutt Mayhew.

Read more like this: Rachael Leigh Cook and Malia Baker on playing Mary-Anne in The Baby-Sitters Club decades apart