Fashion blogger Kim Hutt blends her sharp wit with the sartorial seeds planted in young readers when their wee hands first flipped the pages of The Baby-Sitters Club. What Claudia Wore features the most fashion-forward moments from the series, with the highest praise going to Claudia, and gives us good reason to dust off that bookshelf and get nostalgic.

How did you first conceive of the idea for What Claudia Wore?
I began re-collecting the books when I was living in Wappingers Falls, New York in 2006. I was just down the road from both a Goodwill and a Salvation Army, and they would get huge lots of BSC books. It was a fun little nostalgia trip during a stressful time in my life, and I couldn’t help laughing at how incredibly fascinated I was by the outfit descriptions. 23 years old and just as absorbed by BSC fashion as I was at age eight.

At the beginning, I was just planning on cataloguing each of Claudia’s outfits; there was little to no commentary. Then I started adding a snarky line or two after each description. It kind of snowballed from there.

What have you learnt about yourself from re-reading old Baby-Sitters Club books?
That I needed to get out more! I mean, I’ve always been a re-reader . . . but seriously, I remember this stuff way too well. The other day I was mentally composing a blog entry, and I made a joke about “stupid Andrew Brewer saying ‘hi-hi’.” And then I stopped and corrected myself - “No, saying hi-hi was Jamie Newton’s thing.” It was a frightening moment. This is the stuff I’m dedicating brainpower to. Okay.

Is fashion something you take seriously? Are you looking at The Baby-Sitters Club ironically?
I think that depends on what one considers taking it seriously. I rarely - if ever - keep up with current runway trends, I don’t buy fashion magazines, and I only follow a handful of style bloggers. With that said, are fashion and personal presentation important to me? Yes, very.

I do mock the babysitters quite a bit. Honestly, I’m much more affectionate toward the characters and the series than I let on. Snark aside, I think there’s somewhat of a sense of celebration in this project. I mean, I was seriously emotionally invested in Stoneybrook, long after I’d outgrown the books on an intellectual level. I hope some of that comes through in the blog, even when I’m threatening to throw away every single pair of sneakers Kristy owns.

You also have a blog on Tumblr about Chuck Bass from Gossip Girl, called What Chuck Wore. What would Claudia think about Chuck’s outfit choices?
Oh, she would be so on board! I think she’d really respect his dedication to pastels. Chuck and Claudia are both fashion wild cards in their respective universes; they’re kindred spirits in that regard. (Though, seriously, I wouldn’t let her anywhere near him.) Chuck is more single-minded about his aesthetic (the whole dapper thing) than Claudia is, but I think they both get a big kick out of getting dressed in the morning.

Claudia Kishi was evidently your favourite character - what is it about her character’s approach to fashion that you continue to identify with?
I like that it’s so damn fun for her. Ann M. Martin & the Army of Ghostwriters (I really do think that’d be an awesome band name) often referred to both Stacey and Claudia as trendy, but I feel like Claudia lived pretty far outside the world of trends and fashion currency. I think she would wake up in the morning, say something vague like “I feel cerulean today,” and go from there.

Also she professes a dislike for pink in book #71. I feel that.

What can we learn from Claudia?
Do what you love. Don’t apologize. So you can’t spell and your diet consists entirely of Oreos and Pringles. So what?

What would Claudia wear today?
You know, I like to think Claudia’s look - as hilariously dated as it may seem - is timeless. I’d like to see her in heels - something chunky with a stacked wood heel and hidden platform. I think she’d see a lot of fashion potential in those $12.50 Forever 21 skinny jeans. I could see her buying them in bulk and spending her weekends dyeing, bleaching, painting, studding, and shredding. She’d shake her head sadly at Abercrombie & Fitch storefronts. And she wouldn’t be able to pass a row of candy machines without dropping fifty cents on glow-in-the-dark jewellery. (And probably a gumball or two.)

Top 10 Most Stylish Characters From Children’s Books

10 - The Headless Cupid’s Amanda
She was the creepy stepsister who was really into the occult, remember? Lots of black, veils, bad attitudes, etc.

9 - Sweet Valley High’s Lila Fowler
The original Blair Waldorf. Lila had an amazing wardrobe, mostly because her father felt guilty about his absentee parenting and tried to buy his way into her heart. But really, who needs a father figure when you’ve got a closet full of fabulous designer duds? I mean, Lila was just as well-adjusted as Blair! Oh . . . wait.

8 - Harriet the Spy’s Harriet M. Welsch
She took her spying uniform very seriously, to the point of rescuing a pair of beloved sneakers from the trash (after Mrs. Welsch had the audacity to toss them out). And don’t forget the “black-rimmed spectacles,” which she wore because she thought they made her look smarter. They definitely made her look like a modern-day hipster.

7 - The Baby-Sitters Club’s Dawn Schafer
I know, I rag on her something awful. And the illustrators insisted on depicting her in heinous denim-on-denim ensembles. But every now and then she’d pull out a killer item, like the I’M AWESOME nameplate necklace. Plus, I’ll give her reluctant props for her Madonna phase in book #50. I like a girl who’s willing to experiment. In this case mostly because it gives me something to snark about.

6 - Sideways Stories From Wayside School’s Sharie
Quote: “Sharie had long eyelashes. She weighed only forty-nine pounds. She always wore a big red and blue overcoat with a hood. The overcoat weighed thirty-five pounds. The red part weighed fifteen pounds, the blue part weighed fifteen pounds, and the hood weighed five pounds. Her eyelashes weighed a pound and a half.” Damn, girl, that is a lot of coat.

5 - Just As Long As We’re Together’s Alison Monceau
She borrowed clothes from her actress mom and went around telling people that her dog could talk. This chick was just cool.

4 - Sleepover Friends’ Stephanie Green
Pretty sure the most notable aspect of this entire series was Stephanie’s dedication to dressing only in red, black, and white.

3 - The Unicorn Club’s Mandy Miller
Leukemia survivor. Unicorn Club President. Thrift store goddess.

2 - Harry Potter’s Luna Lovegood
The Claudia Kishi of the wizarding world - totally misunderstood and totally fabulous. Evanna Lynch plays her to spacey perfection in the films. I couldn’t imagine anyone better. And I kinda wanna pair of spectrespecs.

1 - The Babysitter’s Club’s Claudia Kishi
I mean, who else? It had to be you, Kishi. It really did.

- interview by Anna Cipollone