First, some ground rules:
- These outfits are ranked definitively from worst to best.
-All 131 original Baby-Sitters Club series books are included. F$%d the Little Sisters series.
-When more than one person appears, the cover is ranked based on the most noticeable/important outfit, as determined with a special secret science.
- Since Claudia Kishi is obviously a style icon, the bar is set higher for her and she has to work harder to compete with the other girls (at least when they actually put effort into their looks) to prevent her from just completely dominating the top 25. This is also known as the Dancing With the Stars rule.
131. Dawn’s denim-on-denim on Dawn and the School Spirit War
DAWN, NO. No, Dawn. You might have an idea that someone like Kristy or maybe Mallory was the “worst dressed” baby-sitter overall, but you’re wrong. Dawn — hippie, California girl, vegetarian Dawn — was the WORST. I don’t know why Dawn seems to think that being socially conscious has to equal wearing unflattering, personality-free clothes every day of middle school, but she does. This denim tuxedo is just the beginning.
130. Mary Anne’s athletic gear on Mary Anne and Miss Priss
OK, might as well get this out of the way: oversized sweaters/sweatshirts/tops are a MAJOR factor in many of the baby-sitters outfits. It’s almost like Kristy ordered everyone to wear clothes three sizes too big (totally something Kristy would do, to be honest) for the entirety of their stints with the club. It’s ridiculous! Mary Anne takes it way too far here in the interest of contrasting with Jenny Prezzioso’s prissiness, which is actually kinda adorable. Mary Anne’s sweatshirt thing is clearly an adult sized XXL, and her greige sweatpants seem to be tucked into her athletic socks. Totally unacceptable.
128. Kristy’s fair outfit on Kristy and the Mother’s Day Surprise
ELASTIC PANTS, KRISTY?! Even for you, this is low.
127. Stacey’s pink printed shirt over a green shirt The Truth About Stacey
Uh, is the truth about Stacey that she’s actually someone’s dad vacationing in Hawaii? Yuuuuuck.
126. The kid with inexplicably shorter shorts than everyone else on Mallory Hates Boys (and Gym)
Everything on this cover is totally hopeless and it isn’t at all their fault, but that boy with his shorts hiked up to upper thigh level almost rescues them all. I mean, he has sass.
125. Dawn’s inexplicable rolled up jeans / big socks combo on Dawn and the Impossible Three
WTF, Dawn?! Seriously, the big blue chambray-ish shirt is totally legit, but it’s completely ruined by her rolled up jeans and oversized white athletic socks paired with ballet flats. You’re too pretty for this look, Dawn.
124. Abby’s brown and black thing on Abby’s Un-Valentine
Abby is at least trying here, but this “color” combination is just sad. Also, that hat isn’t working for her at all. She reminds me of that weird faux “bad” girl that replaced Kelly for awhile on Saved By The Bell — which is appropriate, since Abby herself is a completely inadequate replacement for Dawn in the final BSC books. Sorry, Abby.
123. Jessi’s button-down and khakis on Jessi’s Horrible Prank
Jessi looks like Jordan Belfort here, smirking just like a Wall Street broker who just convinced you to spend your savings account on worthless stock. A horrible prank indeed. I feel like she probably borrowed this entire outfit from her dad? It’s pretty terrible. Do your laundry, Jessi.
122. Kristy’s baggier baseball outfit on Mind Your Own Business, Kristy
Of all of Kristy’s baseball looks, this one is my least favorite. Somehow she’s dedicated enough to her baseball team to wear an unflattering oversized jersey, but not dedicated enough to pick something more practical than JEANS to play in? You can’t slide in jeans, Kristy. Get yourself to Academy and invest in some baseball pants.
121. Claudia’s jeans and orange t-shirt on Claudia and the Terrible Truth
The most boring outfit Claudia Kishi has ever put on, even though it’s cool how her scrunchie matches her t-shirt.
120. Dawn’s pink two piece swimsuit on Dawn On The Coast
Dawn, look: either wear a one-piece or wear a real bikini. This wishy-washy in-between, high-waisted briefs and sports bra top in shimmery mermaid pink is doing NOTHING for you.
119. Kristy’s gym outfit on Kristy In Charge
It could be worse (see: Mallory), but no one looks good in gym class.
118. Mallory’s ………. on Mallory Pike, #1 Fan
Oh no, Mallory. She looks every bit like a mom going to the grocery store and not one bit like a fun 11-year-old. This also doesn’t look like particularly comfortable bike-riding gear?
116. Stacey’s oversized mom sweater on Stacey and the Mystery of Stoneybrook
Stacey, no. This sweater could have been cute if it was a size or five smaller, or the wool was less chunky, or it didn’t have that hideous random pattern running along the bottom. But it does have all of those things, and it’s terrible.
115. Mary Anne’s elf outfit on The Secret Life of Mary Anne Spier
If I’m being 100% honest I think Mary Anne looks sort of kind of adorable here, but there’s no doubt that this “outfit”/mall Santa escort uniform is the most embarassing thing that a 13-year-old has ever been forced to wear in public. That said, check out that kid over her right shoulder in line — that’s the kind of winter wear I’m talking about!
114. Dawn’s turtleneck on Dawn and the Big Sleepover
Is Dawn seriously wearing a white turtleneck tucked into high waisted jeans? Get it together, Dawn, YOU’RE A TEENAGER. Loosen up a little! Try some colors! Maybe something other than a winter shirt and jeans, sometime?!
113. Stacey’s oversized t-shirt and apron in Stacey’s Emergency
One thing is abundantly clear: Stacey has no idea what size she wears. She’s not even in the ballpark!
112. Mary Anne’s oversized sweatshirt on Logan Likes Mary Anne
Mary Anne’s bow is is cute, but that is definitely NOT the look that won the heart of cute Logan. Speaking of which, his rolled up polo sweatshirt is a lot cooler than Mary Anne’s look.
111. Broken Claudia in Claudia and the Bad Joke
LOL, Claudia looks cooler in a hospital gown than a bunch of other baby-sitters on totally normal days.
110. Kristy’s yellow bridesmaid dress on Kristy’s Big Day
This yellow bridesmaids dress is actually totally fine, especially for a teenager, but Kristy just wasn’t made for dresses and she seems totally out of her element / personal style here.
109. Mallory’s sweater (?) on Mallory and the Mystery Diary
Why is the thing on her sweater the same as the thing on her sleeve?! Is this part of the mystery or what? I’m so confused.
108. Dawn’s pink button-down on Dawn Saves the Planet
I can no longer count the number of times I have said “Jesus Christ, Dawn” while compiling this ranking.
107. Mallory’s windbreaker on The All-New Mallory Pike
Normally people get cooler and more fashionable as they age through childhood, but there’s often a dip just before high school where even the most confident tween goes through a terribly awkward phase. The “all-new” Mallory is the personification of that moment. We are all Mallory Pike, and we’d all rather not think about it.
106. Claudia’s oversized white men’s shirt and jeans on Claudia and the New Girl
Look - the truth is that Claudia always looks great. But we have to hold her to higher standards because of the bar that she sets, and this is just borrrrrriiiiiiiiiing.
105. Dawn’s black cloud on Dawn’s Big Date
Well, maybe the reason your date was a disaster is because you obviously didn’t take it seriously enough to wear something cute instead of that shapeless black whatever-that-is. JESUS DAWN, Lewis clearly likes you and he is a total hottie. Express some personality!
104. Claudia’s peace outfit on Claudia and the First Thanksgiving
Very controversial Claudia look here. I commend her for going out on a limb, but I don’t think this one quite works. It’s mostly the combination of the fit of the shirt and the dainty lacey vest, plus that weird cap thing? And I can’t even tell what’s going on with the bottom. But I do like her giant peace necklace, and I can easily see a strong defense on this outfit. At least she’s got us talking, which I think is always the CK goal.
103. Jessi’s dance uniform on Jessi’s Big Break
There are no less than THREE Jessi-dance-class covers, and this one is the most boring. Her pink and white combo is classic, sure, but she can do better. I expect more from you than this classic ballerina stuff, Jessi.
102. Mary Anne’s little white tee on Mary Anne and the Playground Fight
This could have been a perfectly acceptable, even classic, playground look — a plain white tee and denim cutoffs, paired with Mary Anne’s impeccable short hair? Great! The problem is that shirt is a size too small, and it makes Mary Anne look like a five year old. Seriously, if it wasn’t for the scale she would definitely look like the youngest kid in this picture. She needs to size up and stop wearing her shit from sixth grade.
101. Kristy’s turtleneck onKristy and the Sister War
100. Abby’s purple t-shirt on Abby and the Best Kid Ever
Abby looks exactly like every girl I ever knew in middle school ever, which is precisely what makes this outfit terrible. She’s a fictional character! She can wear whatever she wants! She could dress in prom dresses or tuxedo jackets or just cool-ass leggings, ANYTHING.. and she chose a purple t-shirt tucked into regular fit jeans. Boo, Abby.
99. Jessi’s black and grey turtleneck on Jessi and the Troublemaker
Not digging this look for Jessi — the proportions of the tight fitting but all covering turtleneck and its giant stripes, along with those slighly oversized jeans are just all off, and it doesn’t seem either comfortable OR bangin’. It’s typical little girl stuff, not knowing what looks good together, and Jessi is normally better than that.
98. Mary Anne’s red shirt on Mary Anne In The Middle
What is up with Mary Anne’s age? Sometimes in her post makeover state she looks like she’s 30 and flirty, probably working for some big name media organization in NYC and leaning in and shit, and then in covers like this she looks like she’s approximately 4 years old. While Stacey is testing the boundaries of what 13-year-olds can legally wear, Mary Anne is over here literally looking like one of those creepy child mannequins in J.C. Penneys.
97. Jessi’s red shirt and blue jeans on Happy Holidays, Jessi
In this book, the baby-sitters argue about whether Kwanzaa is racist. The only reason I mention it is because it’s totally inane and yet a lot more interesting than this soulless outfit!
96. Kristy’s red and white striped t-shirt on Kristy and the Secret of Susan
I have nothing to say about this t-shirt. It’s fine, which considering that we’re dealing with Kristy here, means it’s great.
95. Mallory’s red and white striped shirt and jean on Poor Mallory!
Mallory’s family is poor so she’s been borrowing clothes from Kristy, I guess?
94. Mary Anne’s baby walking gear on Mary Anne + 2 Many Babies
It’s completely inoffensive, but seriously, if you passed Mary Anne walking these babies you would definitely think she was a 30-year-old mom, NOT their teenage baby-sitter. Enough with the oversized shirts. ENOUGH!
93. Kristy’s coaching uniform on Kristy and the Copycat
There are a million Kristy-baseball covers and this one falls squarel in the middle. She looks fine and comfortable, all things considered, and at least she’s not wearing stupid jeans. But Kristy looks way better when she’s wearing a more fitted baseball uniform and when she’s not accessorizing with an equally slovenly mini-me.
92. Mary Anne’s Camp BSC shirt on Mary Anne and Camp BSC
I mean it’s fine. Mary Anne sure did get a lot of use out of those cut-offs, and the shirt is charmingly handmade and fits well. Mary Anne’s hair is cute. But wouldn’t it be more fun to tell scary stories at the sleepover camp if she was also wearing comfy pajamas? Maybe a middle school sized footie onesie or something? Just saying, this was a missed opportunity, Mary Anne.
91. Dawn’s letter jacket on Dawn and the Older Boy
OK, Dawn, if you want to wear that letter jacket on your date with 16-year-old Travis go ahead I guess. Your bangs looks funny, but it’s ok.
90. Kristy’s puffy vest on Kristy + Bart = ?
The shade that Kristy is throwing Bart’s hand would be number one if it was clothes, but it ain’t. This outfit isn’t at all Kristy’s worst, nor is it quite her best. She looks warm and comfortable, which is all she cares about anyway, which makes it fine. Bart’s jacket is pretty fly.
89. Stacey’s black and purple get-up on Stacey’s Move
Stacey watched one too many Drew Barrymore movies and thought daisies were cool — the top could be cute with jeans, and the skirt could be cute with a different colored blouse, but paired together it just looks like an ill-fitted LBD. Not a far of her hair either, which always seems to change dramatically within the span of just a few books. Maybe she’s cutting it at home?
88. Abby’s soccer uniform on Abby The Bad Sport
Let’s just appreciate the tagline “Is Abby a super jock or a super jerk?” for a second before we move on. ………… OK, that was fun. So, this is just fine! Abby manages to look a hell of a lot cooler than creepy lion-faced Abby lookalike who’s mad at her while wearing basically the same outfit with more white. I think it’s her shorter shorts and untucked jersey, the soccer styling of cool girls everywhere.
87. Claudia’s floral tunic on Claudia Makes Up Her Mind
Not my favorite Claudia outfit, but brown jeans are a bold move and her tunic looks cool in a thrift score kinda way. It’s fine! If one of the other baby-sitters was wearing this it would probably be one of their best outfits.
86. Kristy’s stripes on Kristy and the Dirty Diapers
Kristy’s look here is presentable, which is all we can really ask of her, although I dare you to try to figure out what’s going on physically with her right leg/lower half here. The Doc Marten style boots look amazing on her and compliment her personality perfectly — not sure why she’s not wearing those every day. I find the pink socks and scrunchie out of character, however — did Mary Anne give her those for Christmas or something?
85. Mallory’s green and gold outfit on Kristy’s Worst Idea
You know it’s a big fight because everyone couldn’t be bothered to dress like they give a shit about each other / themselves / the world. Seriously, when Mallory is the best dressed girl in a collection of seven baby-sitters, something is seriously wrong. I do like her golden khakis, though. She looks like an ’80s businesswoman, which would be cooler if she wasn’t a 13-year-old.
84. Jessi’s purple top and jeans on Jessi’s Secret Language
Jessi had better outfits, but I can dig her fitted and tucked in top and mom jeans, and I like how Matt Braddock has his polo tucked in to match.
83. Dawn’s cuffed denim on Dawn and Too Many Sitters
Pretty good outfit for Dawn “Which Baggy Ass Tee Should I Wear Today” Schafer. Her shorts are cute enough, although v. dated, and that shirt looks good on her. I don’t approve of the half talk situation, but it’s Dawn we’re talking about so obviously she can’t look too “put together” or else someone will revoke her California hippie ID card.
82. Stacey’s cleaning outfit on Stacey McGill, Super Sitter
So apparently the baby-sitters just have one cute thrifted apron that they pass around amongst themselves for miscellaneous birthday projects. But Mary Anne (see below) pairs it perfectly with cut-off shorts while Stacey just throws it over a giaaaaant sweater that’s bound to get splashed with bleach, and those jeans need to be hemmed bad.
81. Claudia Kishi’s v-neck on Claudia Kishi, Middle School Dropout
I was thinking this Kishi outfit was kind of underwhelming, but it really grows on you. The color combination — denim, chocolate brown, and an army green scrunchie — is the perfect palette for fall, and her big hoops are totally classic.
80. The little Miss Stoneybrooks in Little Miss Stoneybrook… And Dawn
Hard to choose a favorite girl here, but Mallory’s little sister Margo Pike (in the green) is awfully sassy. I’m pretty into her medium-length sleeves and ruffle situation.
79. Whichever one of Mallory’s little sisters is wearing a nurse hat on Get Well Soon, Mallory!
Mallory with mono = boring. Clipboard girl = boring. That sassy ass little nurse = FABULOUS.
78. Claudia’s blue and white ensemble and side-ponytail on Good-bye Stacey, Good-bye
Lot going on on this cover but it’s all pretty boring until your eyes land on Claudia Kishi’s high side-ponytail. It’s off the hook, obviously.
77. Claudia’s sweater on Claudia and the Phantom Phone Calls
I mean, it’s a great sweater. but Claudia looks so conservative on this cover compared to her later efforts that it’s hard to commend her on those weird robot-like shapes.
76. Stacey’s mom on Stacey McGill… Matchmaker?
Stacey’s mom is stepping out with a nice looking fellow and she looks foxy! The BSC could stand to learn from this look — it’s classic but not without personality. Stacey’s mom also looks approximately 20 years younger than Stacey herself, who is definitely pulling off a strong ’90s mom vie with her mid-waisted jeans and autumn sweater.
75. Claudia’s loosely tied pink button-up on Claudia and the Genius of Elm Street
This look is super cute - love the calf length denim skirt situation - but given Claudia’s prowess with an outfit, it just feels like it could be so much more. Maybe some bangles or a different kind of undershirt? But it’s super cute, really… Just a little disappointing for a Claudia book.
74. Kristy’s giant green sweater on Kristy and the Worst Kid Ever
I don’t expect much from Kristy — she’s reliably disappointing when it comes to clothes — but because the bar is set so low, I find myself looking for something to love in everything she wears. And after careful consideration, a decision has been reached regarding this sweater: it’s alright. It is soooooo oversized that it crosses the line from sloppy to deliberately comfortable, and the olive green ages her just enough that she could pass for your a college-age poetry major with a particular interest in Emily Dickinson.
73. The guy in the background with the pink and white fedora on Jessi’s Gold Medal
Red synchronized swimming suits don’t do anything for me but that dude in the white and pink fedora probably has a few thousand riding on this competition and he looks awesome.
72. Stacey’s math competition outfit on Stacey The Math Whiz
Looks like Stacey finally got some fashion tips from her mom and/or just raided her mom’s closet for looks. She looks great, this is perfect “making math cool” gear.
71. Claudia’s blue and silver stripes on Claudia and the Great Search
That color-coordinated scrunchie really makes this outfit, although Queen Kishi is ALMOST overshadowed by Emily Michelle’s pink on pink on pink hot air balloon sweatsuit.
70. Mary Anne’s cleaning outfit on Maid Mary Anne
So, Mary Anne looks totally adorable even when cleaning house. Her apron was clearly thrifted at the Stoneybrook Goodwill, and she probably cut some of the trademark BSC mom jeans into flirty cutoffs all on her own. Plus that bandana in her hair is sassy as hell. Post makeover Mary Anne is the best, y’all.
69. Emily Michelle’s yellow overalls on Kristy for President
Look, I really do feel bad that tiny Emily Michelle keeps outshining Kristy on Kristy’s covers but you can’t deny that the combination of political-themed hat, yellow overalls, and tiny green t-shirt is a lot more exciting than the blue on blue zzzzs fest that Kristy has on. EM is rocking that look and I’d wear it in a heartbeat. P.S. the St. Bernard’s outfit is also more exciting that Kristy’s. Sorry.
68. Stacey’s purple bikini on Mary Anne And Too Many Boys
Sorry Mary Anne, but your one-piece and bad posture isn’t cutting it next to Stacey’s perfect tie front bikini. How did Stacey even get away with that on a baby-sitting trip?! Also, I always thought this title was an oxymoron and it still is!
67. David Thomas’s chicken outfit on Kristy and Mr. Mom
I don’t remember why Kristy’s little brother is wearing a chicken outfit and honestly I don’t really care. What I do know is that the attention to detail involved in putting feather shapes on his upper arms, as well as the perfect shape of that tail, is the work of a truly talented costume-maker. Kristy’s green turtleneck didn’t stand a chance.
66. Jessi’s dance outfit on Jessi and the Dance School Phantom
Jessi’s just wearing standard, boring ballerina gear but DEM TIGHTS are the most perfectly ladylike dance class color that I’ve ever seen in my entire life. Is that a subtle ombre effect? Chills.
65. Dawn’s pink sweater on Stacey’s Choice
This is classic ’90s girl wear — light blue jeans and a big soft sweater, completed by a medium coke. Dawn stands out on this cover because pastels in the winter are always a bold choice.
64. Dawn’s cuffed shorts on Dawn and Whitney, Friends Forever
Significantly cuter than the last time we saw Dawn in these shorts. She clearly learned some belting tips from Claudia before she moved to CA.
63. Laine Cummings on Stacey’s Ex-Best Friend
Let me be clear: Laine is a heinous bitch who is horrible to Stacey, called her boyfriend “Heart” and makes fun of the baby-sitters. She’s a horrible person. But there is NO DENYING that on this cover, she is the coolest person in the shot. That’s her sulking on the far right. Blazer, sweet patterned top, pearl earrings, perfect ’90s bangs? Yeah, sorry BSC but your oversized sweatshirts just aren’t cutting it in this shot.
62. Dawn’s big stripey pink tee and jeans on The Ghost at Dawn’s House
I’m actually pretty into this shape for Dawn - an oversized, boxy shirt and skinny jeans, well before their time. She could have stepped up her shoe game but this isn’t bad considering how bad her taste usually is.
61. The hot teacher on Don’t Give Up, Mallory
Wow, totally crushing on this Gosling-esque teacher in his khakis and casually rolled up sleeves, sitting on the desk like “sup kids?” Mallory doesn’t stand a chance.
60. Abby riffing on Alice in Abby in Wonderland
It’s a classic, but this outfit would be cooler if she was wearing some kind of updated/modern version instead of a precise replica of Alice’s dress. but it’s cute and her hair looks better than usual. Still, imagine with me if Claudia Kishi got this cover, and we were looking at Cheshire Cat inspired stripes and a tiny top hat. Sigh.
59. Emily Michelle’s colonial onesie on Kristy and the Baby Parade
Kristy’s outfit gets a pass / ignored because it’s a period costume and she’s Kristy, but I’m actually pretty obsessed with what her adopted sister Emily Michelle is wearing here — a ruffle-fronted pink onesie paired with purple mary janes. Is it weird to want to wear this as an adult?
58. Claudia’s vest on Claudia and the Little Liar
Claudia’s look here is carried entirely by that orange beaded necklace, wich seems to match the buttons on her grey-green vest. That’s dedication. Also, as ever, big fan of those hoops.
57. Mary Anne’s lilac shirt on Mary Anne To The Rescue
Mary Anne is working that lilac, but the star here is her hair. Post-makeover Mary Anne’s hair is so cute that she’s almost overshadowed by it. All I can see is her hair. Is that a good thing?
56. Claudia’s waiter fantasy on Claudia and Crazy Peaches
Peaches always made me a little uncomfy (she is too old for this), but Claudia all dressed up in a waiter outfit is totally adorable. She is even better when she wears business suit elements in her own personal outfits, but she manages to imbue even this classic getup with her own flair, just because she is her.
55. Mary Anne’s windbreaker on Mary Anne and the Memory Garden
The jacket is nothing to squeal over, but it will do. It’s those dark denim pants and brown loafers that are working for Mary Anne, and pairing the office look with that jacket keeps her looking young and fresh (but not too young. Lastly, her hair looks amazing — as always.
54. Kristy’s long sleeved stripes on Kristy Thomas, Dog Trainer
Aww, Kristy looks cute here! Those jeans fit her really well and the fairly fitted long-sleeved t-shirt shows a moderate amount of thought and care put into choosing her clothes. Plus, true fact: everyone looks better when they’re petting a dog.
53. Mary Anne’s pastel color palette on Mary Anne’s Bad-Luck Mystery
The soft fabrics and conservative neckline here are standard Mary Anne material, but that sea foamy turquoise next to those girlie pink jeans?! TO. DIE. FOR.
52. Mary Anne’s pink sweater on Mary Anne Breaks the Rules
Is Logan 20 years old in this picture?! Oh well, he’s foxy and Mary Anne is wearing the perfect “invite your boyfriend to your baby-sitting gig” outfit, managing to look both responsible and completely kissable.
51. Claudia’s yellow skirt and stripes on Farewell, Dawn
Maybe Dawn should have chosen a more memorable outfit on her last day in Stoneybrook, but she didn’t. Also, how come Kristy and Claudia look so happy and Mary Anne is the only person who’s appropriately bummed? Aaaaanyway, Claudia steals the spotlight again. She’s wearing a super cute stripey vest and a buttery yellow skirt, and super hot brown boots. Love, love.
50. Dawn’s purple and yellow suit on Dawn and the We Love Kids Club
OK, so when Dawn moves to California she joins her friend Sunny’s copycat baby-sitter’s club and they just have the BSC there, except everyone (everyone!!) is blonde. In my actual experience it’s not true that every girl in California is blonde, but whatever. Anyway, the descriptions make it almost impossible to tell each We Love Kids Club member from one another, so I’m actually not 100% sure that’s Dawn wearing a suit in the foreground. If it’s not, someone else is stealing her cover because that girl has sass and is wearing a totally appropriate-for-13-but-cute swimsuit while apparently speaking on a giant pink phone next to a waterfall. Pretty cool!
49. Abby’s Twin
Love the colorful jeans, those are perfectly appropriate for a kid and yet cool enough that adults would find themselves drawn to the Juniors section to examine them and then put them back on the rack, realizing that they would look totally ridiculous at the office.
48. Jessi’s shiny black leggings on Jessi and the Bad Baby-sitter
Abby, take note: this is how you make brown + black work. These black shiny leggings are totally working for Jessi, even though this is obviously a super casual, interviewing new terrible baby-sitters look.
47. Kristy’s yellow flannel on Stacey vs. the BSC
I never thought the day would come that Kristy would be the cutest girl on an all baby-sitters cover but here we are. That yellow and black flannel is ADORABLE, and are those skinny jeans? She’s probably listening to riot grrl bands in secret. Proud of you, Kristy!
46. Claudia’s black vest and skirt on Claudia’s Big Party
Another book, another adorable Claudia outfit. It’s almost boring when she’s perfect. But not really, that vest is clearly from a men’s suit and she pulls it off like a champ.
45. Stacey’s green number on Stacey’s Big Crush
If this was a ranking of facial expressions, Jessi’s “nope” face would be #1, but instead we’re talking about Stacey’s green dress, which looks a liiiiiiitle bit like it was made out of curtains by someone’s magical nanny, but is still pretty darn cute all things considered. Don’t think it’s going to impress that overdressed 22-year-old, though.
44. Dawn’s sweatshirt situation on Dawn’s Wicked Stepsister
Trouble in paradise for Dawn and Mary Anne, who are also competing here for cutest look. Dawn wins out due mostly to the fact that Mary Anne is wearing mom jeans. love that sweatshirt, Dawn. It someone manages to convey that you’re from California while also being warm enough for chilly Stoneybrook
43. Stacey’s beach swag on Boy-Crazy Stacey
I honestly can’t quite figure out what Stacey is wearing here — is that a really cute dress that’s a little weird for the beach, or just a t-shirt / cover-up? Either way, the flirty length paired with the practical wind-breaker is hot. No wonder that lifeguard is eyeing her.
41. Abby’s black dress on Abby’s Lucky Thirteen
Abby’s goth dress is pretty tight. I wish she was really goth, there’s a whole alternative universe with a real goth baby-sitter that would have been super awesome, but unfortunately I guess she just thought this is what fancy clothes look like. Anyway, goth suits her. GothAbby forever.
40. The bad girls on Stacey and the Bad Girls
Those bad girls were the only people in all of Stoneybrook actually dressing like they lived in the ’90s. Stacey looks fiiiiine, but those girls and their flannel look like they smoke cigarettes and listen to Nirvana on their Walkmans. Pretty sweet, bras. She should introduce them to Kristy.
39. Abby’s velvety dress on Welcome To The BSC, Abby
Even though Abby showing up in book #90 was a little too late for her to become anyone’s favorite character, she looked really cute in her debut. This short velvety and lace dress is adorable and weird, her tied pearl necklace was ahead of its time, and the black tights and wedges really pull the whole thing together.
38. Mary Anne’s little red dress on Dawn’s Family Feud
One of the few times Mary Anne wears the color she’s most flattered in, red. She looks so sassy here, and the white flats are the perfect touch. Her dress is certainly a lot cuter than the glorified t-shirt that Dawn is wearing.
37. Jessi’s patched-up jeans on Jessi and the Superbrat
Jessi’s jeans rule. We’re all so caught up with Claudia’s style that it’s easy to forget that Jessi had super personal style at age, like, 11 or whatever. She looks awesome.
36. Claudia’s personalized shirt on Claudia and the World’s Cutest Baby
Um, Claudia has a pink bowling shirt that has her own name on it?!?!?! Claudia is the coolest, she can’t even be outshone by that baby’s tiny Claudia ponytail.
35. Claudia’s vest and many necklaces on Claudia, Queen of the Seventh Grade
It would be nice to be able to see PopularClaudia’s whole outfit, but this white blouse / black vest / 3 necklaces look is classic Kishi and she looks awesome (and also 20000x cooler than any of the “popular” girls I knew in middle school ever, but that’s neither here nor there).
34. Stacey’s little spring dress on Stacey’s Ex-Boyfriend
Stacey clearly knows what to wear on “ex-boyfriend comes over and sits morosely in your chair for no reason” day. That flirty floral dress will definitely make him regret his poor decisions. Cute sandals, too!
33. Jessi’s short-sleeved flannel on Jessi’s Wish
Dude, we need to talk about how often Jessi’s looks are totally on point. Like right here she is doing this masterful played down tomboy thing, like Kristy, if Kristy wasn’t so singularly determined to repel any romantic attention whatsoever. Other times she channels a Claudia Kishi punk look, or a Dawn ease. Is Jessi just the best of the BSC combined into one perfect being? Something to consider.
32. The snobs on Kristy and the Snobs
Sorry Kristy, but the snobs are the star of the show on this cover. That orangey-red skirt / royal blue combo? That mustard yellow sweater vest?! THAT CAT?! The snobs were jerks but they knew how to pick out an outfit.
31. Mary Anne’s pink explosion on Mary Anne vs. Logan
The pink winter puffiness (down to her gloves!) is amazing, but what’s even better is how well it’s complimented by Logan’s puffy green jacket. Oh and then they broke up. Heartbreak city, man. But at least Mary Anne still owns the cutest beret in the world.
30. Stacey’s cheerleading outfit on Stacey and the Cheerleaders
There’s little more classic than a good cheerleading outfit and Stacey and her charge are just perfectly endearing here, straight out of some pervy Tom Wolfe novel about competitive cheerleading. Adorable, but secretly edgy.
29. Claudia’s purple suspenders on Claudia and the Sad Good-bye
Claudia completely pulls off these purple suspenders and sapphire-y green silk top, even as she spends her last minutes with her beloved grandmother mimi.
28. Stacey’s train farewell outfit on Stacey’s Broken Heart
Adorable. Those short little brown boots really make this outfit, which is somehow mature and yet not mom-ish, a true feat for any baby-sitter apparently. Her skirt is adorable and the scarf is the perfect touch. Plus Robert’s flowers match her outfit perfectly. This moment will probably flash before both of their eyes before they die, so thank God Stacey looked presentable.
27. Jessi’s legwarmers on Jessi and the Awful Secret
Jessi has catapulted her dance studio look from a 7 to a 9 with the addition of those giant blue knitted legwarmers complete with matching headband. On point, as usual.
26. Mallory’s pink/yellow combo on Mallory on Strike
Well holy shit, if it isn’t Mallory Pike actually wearing a real OUTFIT! This is a pretty cool look,. Never would have paired fuschia with butter yellow myself but somehow it miraculously works and even defies the conventional wisdom about redheads and pink. She looks great AND super comfortable and even her hair looks like it might have had some product applied to it. Good job / good effort, Mallory!
25. Mary Anne’s bob on The Fire At Mary Anne’s House
The last BSC book didn’t do much in terms of outfits — Mary Anne’s probably wearing what she sleeps in and it’s burned to shit, which is just sad. But let’s be real, the star of this cover is Mary Anne’s slightly grown out short bob, which is SO CUTE. Her haircut was prooooobably the blueprint for Amelie’s iconic ‘do. Can I take this picture to my hairdresser without seeming totally insensitive about the fire at Mary Anne’s house?
24. Shannon Kilbourne’s purple and red ensemble on Kristy’s Mystery Admirer
Another book, another opportunity for Kristy to be completely upstaged by a minor character on the cover. Associate member Shannon Kilbourne is about 1000000x more interesting that Kristy on this cover. That pleated skirt paired with the purple sweater vest? Perfect. P.S. Kristy, are those pineapples or waffles on your sweater?
23. Mary Anne’s little green patterned dress on Mary Anne and the Great Romance
This is the BSC book where reality jumps the shark a bit and besties Dawn and Mary Anne get to become stepsisters. But that’s not the point here: Mary Anne’s dress is. It’s adorable! Kind of a ’60s mod inspired vintage look, flirty but not inappropriate for the whole mom’s wedding scenario.
22. Tess’s pink overalls on Stacey’s Secret Friend
So the plot of this book is like, Tess is weird and the kids call her Swine-heart the Destroyer (?!) because she dresses lame and then Stacey tries to help make her over and then she finds out that Tess grew up in Paris (cool) and that all her friends there dress like this (because they are cool). Whew. All of which makes perfect sense because on the cover of this book, Tess is so clearly the coolest kid at school and the only one of the girls you’d even bother to hang out with in the first place. Pink overalls with a pink flowered shirt underneath, plus thick-framed black glasses?! Tess is a badass and Stacey needs help. Also, LOLing at that girl in the background with a denim vest and denim jeans.
21. Mary Anne’s blue trenchcoat on Mary Anne and the Little Princess
You can’t really tell what MAS is wearing underneath this coat, but if I could own one single item from the baby-sitters’ closets, I might choose this. Those giant pockets are perfection. Her little chunky heeled loafers are sharp too, as is that chauffeur guy’s suit.
20. Claudia’s oversized sweater on Claudia and Mean Janine
Claudia Kishi’s oversized sweaters were always on point, and this one is definitely a favorite. Janine gets no points whatsoever. Who wears those colors together?
19. Kristy’s baseball uniform on Kristy and the Walking Disaster
This is Kristy at her best: comfortable, happy, and on a baseball field. She’s in the 99th percentile of looking good in a baseball hat, her hair has that dirt-induced natural wave, and her handmade Kristy’s Krushers t-shirt is just adorable.
18. Mallory’s green and pink ensemble on Mallory’s Christmas Wish
Mallory is legit adorable here with her neon play on Christmas colors, short skirt, and super soft looking greem sweater. Pulling off sneakers + a short skirt is hard to do, but she manages it. Overall, one of her best showings ever. Maybe relating to Mallory isn’t so bad after all.
17. Claudia’s jaunty cap on Dawn’s Big Move
Show me a cover of all the baby-sitters, and I’ll show you a cover where Claudia Kishi is all that matters. Those boots, that floral, her weird hat, giant earrings, all of it. I hope those other boring girls know that they are in the presence of greatness. P.S. Stacey looks hot too.
16. Jessi’s green and turquoise ensemble on Jessi Ramsey, Pet-sitter
OMG, JESSI. Those pants! I would kill for them, not to mention the balls it takes to pair that color with olive green and actually pull it off. She looks hot and it’s a shame that entire outfit is about to be covered in the fur of miscellaneous animals.
15. Claudia’s baseball outfit on Claudia’s Freind Friend
OMG, Claudia just took Kristy’s whole boyish baseball thing and SCHOOLED her on it. The thing about Claudia is that she can wear thing that might look lame on other people and sprinkle her magical Kishi fairy dust / jewelry on them and make them actually look cool. The tucked in / belt situation and the necklaces really make this one work in a deep way.
14. Mallory’s horseback riding outfit on Mallory and the Dream Horse
So this is awkward but it turns out that Mallory’s best outfit of all is just her standard English horseback riding gear. That classic uniform is just rock solid and Mallory’s entire adolescence couldn’t come up with anything better. It would be sad if she didn’t look so awesome in that olive blazer and those shiny boots.
13. Claudia’s western outfit on Claudia and the Middle School Mystery
Only Claudia Kishi is capable of making a brown’s men’s vest and short sleeved button up look this cool. She looks awesome — like a glorious hybrid between Hey Dude and Indiana Jones, but keeping her scrunchie high and her jeans tight to emphasize her feminine side. Perfect outfit and way too cool to worry about school.
12. Mary Anne’s running outfit on Mary Anne and the Search for Tigger
Those leggings are dope as hell. The socks look good. The oversized sweatshirt is the ultimate compliment. The long pigtails are cool. But again, most importantly, THOSE LEGGINGS! Side stripe filled with random shapes? Would wear.
11. Kristy’s baseball uniform on Kristy At Bat
The best Kristy has ever looked, period. Her baseball uniform fits better than most major leaguers wear them these days, she has her socks pulled up perfectly, and most importantly, she’s comfortable and happy and expressing what she loves.
10. Stacey’s hearts and checkered leggings / Claudia’s overalls on Kristy’s Great Idea
It’s hard to pick a favorite outfit on the cover of BSC #1 but amazingly, Claudia’s cool ass jumpsuit/overalls are actually overshadowed by Stacey’s late-80s rights and sweater combo deal.
9. Claudia’s boy catching dress on Claudia and the Perfect Boy
More like CLAUDIA AND THE PERFECT OUTFIT, am I right? Claudia knows exactly what to wear on a date and it is this scandalously short, witchy black number. Give her 10 years and she’ll be stopping traffic whenever she feels like it.
8. Stacey’s Cher Horowitz esque look on Welcome Back, Stacey!
Damn, Stacey came back from New York all grown up and looking sharp as heck. I didn’t even notice what Claudia was wearing on this cover because Stacey looks so grown-up and beautiful and cool. That skirt? Those flats? To die for.
7. Claudia’s roller-skating outfit on Mary Anne Misses Logan
Outfits like this one are why Claudia Kishi is truly the queen of fashion. While the other sitters are wearing cute stuff as well, it’s Claudia who had the guts and glory to wear a fucking purple fedora and matching vest to the skating rink. Claudia set a standard in personal, unique that thousands of girls strived to pull off and failed miserably. Here, she shows us all how it’s done right. Bravo, Claudia. Where did you get those leggings?
6. Mary Anne and her new haircut on Mary Anne’s Makeover
Much like Miley Cyrus, Mary Anne got like 1000x cooler and edgier the moment she chopped her hair off. She went from being the sweet innocent baby-sitter to being a cool but still girly fashion icon. Even Claudia’s fashion cross in the background can’t compete with those floral leggings and her androgynous cut.
5. Claudia’s tuxedo jacket on Claudia Kishi, Live From WSTO!
Remember how Claudia Kishi is in MIDDLE SCHOOL? She’s a CHILD and she dresses cooler than 99.9999999% of adults I’ve ever met in my life. This tuxedo jacket paired with a high waist is just bitchin’. Claudia Kishi: the coolest 13 year old on planet earth.
4. Jessi’s Punky Brewster esque purple and orange outfit on Jessi’s Baby-sitter
Jessi’s underrated personal style shines through yet again. That sweater is nuts in a good way, the skirt is the perfect length, the yellow turtleneck peeking up is adorable, and she’s wearing PURPLE SOCKS OVER ORANGE SOCKS. Jessi: to me, you are perfect.
3. Mary Anne’s flawless ketchup and mustard ensemble on Mary Anne Saves The Day
This super iconic Mary Anne cover does the impossible: it makes a yellow turtleneck look cool. Those pigtails, that velvety looking long skirt, those cable-knits… Damn.
2. Stacey’s beach attire on Stacey’s Lie
OMG, Stacey! She looks amazing here — actually a little too amazing when you consider that she is 13, but whatever. That skirt is so cool! It’s the perfect length for the beach, leaving her ankles free to get wet and salty, and her cropped tank was totally on trend and yet timeless. She looks happier than she ever has, and the guy is cute too. Get it, Stacey!
1. Claudia “Bow Down Bitches” Kishi on Keep Out Claudia
Nothing I could say could possibly add to the sheer perfection that is this outfit. Beyonce probably wrote ***Flawless about this cover.