The Artist Who Draws All Her Daughter’s Outfits

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For the past two years, Williamsburg-based artist Jenny Williams has documented her 12-year-old daughter Clementine's outfits, as well as those of her two sons, and many of her daughter’s friends, almost daily. The resulting illustrations — colorful sketches of tweens wearing playful, zany, and largely un-self-conscious outfits — are the subject of her popular blog, What My Daughter Wore. This week, powerHouse releases a new book of the same title, featuring highlights from Williams's blog as well as new illustrations.

The Cut spoke with Williams about what inspired her to start the project, her daughter’s own evolving style, and why she dressed as a Victorian orphan as a kid.

What was it about your daughter’s dressing habits that intrigued you?
I think that she’s very creative and very unique. She never took much input from me — I dressed her for the first year or so, but ever since she was about 1 1/2, she’s had her own ideas about how to dress. I remember there was an entire year when she was 2 or 3 that she only wanted to wear a Danskin leotard — a convenient thing right around toilet training.

How would you describe her style now?
It’s kind of whatever strikes her fancy. To me, it was interesting and poignant the way she would get dressed to express something about how she’s feeling. She has a sort of off-kilter way of thinking about most things in the world, including the way she dresses. She has a lot of hand-me-downs from her older brothers and a lot of vintage. It’s a mix-and-match kind of thing. I would say, though, that it’s become a bit more conventional as she’s gotten into her tweens, and into the middle-school years, which is a little bittersweet.  

So what does she wear now?
Skinny jeans. Although she did borrow a pair of my jeans yesterday, which are very slouchy. But mostly it’s skinny jeans, leggings, Doc Martens.

What about your other kids?
The way that all three of my kids dress could not be more different. My oldest son, who’s 22, dresses in found clothing on principle. And my middle son could care less. He wears T-shirts from national parks that his friends have brought back from vacations and jeans.

How do you choose who to draw?
It’s totally just based on my reaction to what they’re wearing and how they look. On the surface level, the project is about making drawings of interesting outfits that kids are wearing. There’s a more emotional tide to it for me that it’s also recording the passage of time of my own daughter and the kids that I draw on a regular basis. It’s got a time-capsule element to it.

Do you remember what your own style was like as a kid?
Yeah. When I was in middle school, I was definitely an outsider and an eccentric. My best friend and I dressed like two Victorian orphans. [Laughs.] It was definitely a way of setting myself apart from everyone else.

Do you think your blog and book have changed your daughter’s awareness of the way that she dresses?
I would say no, but I could be wrong. The other day, she overheard me saying that I thought she was kind of indifferent to the whole thing, and she corrected me and said she’s very excited about it. So it may influence her more than I think it does, but to my eye, she just does her own thing.  

How much longer do you think you’ll keep drawing her?
I mean, from the time my kids were born, I’ve always drawn them privately, for myself, and I’ll always be doing that. In terms of this project, I don’t know how much longer I’ll be doing it. It may have run its course at some point soon. I don’t know. But I’ll always be drawing her.

Photo: Jenny Williams/Courtesy of PowerHouse Books
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