What 11 People Are Wearing on the First Day of School

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What you wear on the first day of school can set the tone for the whole year. Whether you’re a first-time student or a teacher who’s been in the business for decades, chances are you’re probably going to give at least some thought to what you’ll be wearing when you enter (or reenter) the hallowed halls of learning. We asked a bunch of people living in New York City about their own outfits and what they’re looking forward to in the coming year.

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The Grad Student

Name: Anneliese Cooper

Age: 25

Where she’s headed: Her first year in the nonfiction MFA program at the New School.

What she’s wearing: “I bought the skirt at Marshalls — it’s Cynthia Rowley. The most important thing about it is that it has pockets.

And this is one of my power shirts. I’ve had it since high school. This album is called “Raw Power,” and the band is The Stooges. I have a couple shirts that are like this; they’re all band T-shirts, and you feel the energy of the band with you.

I found these shoes outside of my friend’s apartment in 2012. They’re just now starting to fall apart. I’m going to wear them until they crumble.

Then, last but not least, the bra is from this great company, JBC Lingerie. They’re handmade in Australia. My friend bought one but it was the wrong size, so I bought it from her.

I was prepared to go to school not wearing it. But I’m coming into myself as a person a little bit more intentionally. For a very long time I was like, ‘I don’t have the kind of body that people tell me I’m allowed to dress.’ I used to dress in a very armored and super closed-off kind of way. And there’s something about wearing a super cute, fun bra! I’m claiming a little bit of this pretty, sexy kind of thing. Also, the bra allows me to keep the shirt off-the-shoulder enough that it sort of emerges from the waistband of the skirt.”

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The Preschooler

Name: Christian Pabon

Age: Turning 4 in September

Where he’s headed: His first year of pre-K in Bed-Stuy, Brooklyn. “I’m a little nervous about my new school!” he said.

What he’s wearing: Gap jeans (“They ripped because of all his running around,” said his mom, Mikaela), a hand-me-down T-shirt, and Stan Smith sneakers from DSW. According to Mikaela, Christian likes to pick out his own shoes. According to Christian, “THESE ARE MY FLYING SHOES!” He proceeded to jump up and down.

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Bonus: The Turtle

Name: Mr. Turtle

Where he’s headed: To pre-K with Christian.

What he’s wearing: A shell, custom fit.

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The Newly Minted Drama Teacher

Name: Britt Goodman

Age: 28

Where she’s headed: Her first year as a drama teacher at a high school in Ozone Park, Queens. Britt underwent a career change recently: “I came to New York to work in professional theater, and I worked as a stage manager and I’ve worked in theater offices and all sorts of things. And then a couple of years ago, I had some personal family/life stuff happen. I reevaluated what I wanted to do, and I decided to go into teaching. I just graduated [from NYU’s theater education program] this May.”

What she’s wearing: “When I was little, the first job I wanted was to be a costume designer. And actually, when I was thinking about what I wanted to transition to after professional theater, I looked into the costume programs at FIT, and then after talking to them, they were like, ‘You will not get a job.’

There’s so many things you have to think about, especially as a theater teacher. You have to be able to move. You can’t be sexualized in any way. Even with high schoolers, I’m moving around, I have to be able to kick. I’m on my feet all day. Even when I want to sit down, I’m on my feet. I have to have pockets. And I have to be comfortable.

I also always get cold. I’m going to have to have a blanket or sweater situation and I’m going to look ridiculous. A lot of people have been saying that I look younger than I am or that I look really chill. And I have a feeling it’s because an oversized white shirt has really been my staple recently. This one is from COS and I got it for 70 percent off. It had to be $30, and it’s originally, like, a hundred [dollars]. And then I actually also got these pants from COS. They were also 70 percent off. I just like the crisp look because I want students to come in and feel relaxed but also know that I’m the teacher!”

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The Family

Names: Emily (L), Allison (C), and Maddie Beggs (R)

Ages: Emily is 12, Allison is 45, and Maddie is 10.

Where they’re headed: Emily and Maddie are entering eighth and sixth grades at a middle school in Connecticut; Allison is starting her eighth year of teaching at a different middle school, also in Connecticut.

What they’re wearing: Emily is wearing a top and skirt from Target. “I like sparkly things!” she said, and as for the headband, “It was [Maddie’s], but she doesn’t wear it anymore.” She’s looking forward to no longer being in seventh grade — “You’re not the youngest, but you’re also not the oldest.”

As for Maddie, who’s wearing hand-me-downs from Old Navy, “I like this because it’s just normal clothing — I don’t like to dress up.” She’s looking forward to “being in a whole different school, having a whole new experience.” And, of course, “being with [Emily]!”

Allison is also wearing a dress from Old Navy. “I just need to be comfortable,” she said. “I’m on my feet all day! And usually at this time of year, it’s still pretty warm in the building.” And of the upcoming year, she said, “I’m hoping this year is calm; the past couple of years have been hectic for me with teacher shuffling in my department. I also teach art and am looking forward to turning out a couple of new projects. And seeing my work friends!”

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The Teacher Trainer

Name: Brian Johnson

Age: 33 (the shoot took place on his birthday!)

Where he’s headed: Back to his job at Lit Life as executive vice president of growth and expansion. Brian explained: “We go into the classroom and we actually co-teach with the teachers. We look at the curriculum to make sure that titles are diverse and affirming to the student population in schools. We do this nationally. I want to make sure all kids, no matter if they’re black, white, rich, or poor, can read and write.”

What he’s wearing: “Tennis shoes are essential ‘cause you’re running around the classroom, you’re in and out. These are just old-school Adidas. I love a pop of color, so I love my pink and green polka-dot socks from H&M. The pants are camo, but you wouldn’t notice that it’s actually camouflage; they came from Zara. The button-down is from Uniqlo. I think they have just great, affordable clothes. And then this... vest? Cardigan, -ish? This is from ASOS. You can be a teacher and have a little funk. And it’s still professional, and it still looks good.

The bracelets are from a place in Brooklyn called Nicholas Bookstore. Especially as a teacher, you’ve got to stay grounded. So all of the materials that are used, like tourmaline and zinc, are materials that help you with focus. If you want enlightenment, if you want joy, they have jewelry for that. It has a little bit of purpose.”

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The Special Education Teacher

Name: Emma Schaeffer

Age: 27

Where she’s headed: Back to a school in Harlem, Manhattan for her fourth year of teaching. Emma said that her students “have what would be classified as mild to moderate special needs, as opposed to severe. So we have a lot of kids with learning disabilities, a lot of kids with behavioral disorders. Many with both of those things. Some of them fall on the spectrum. Our classes are really small — the younger kids are in classes of six — and there are two adults, a teacher and a TA, in every class.”

What she’s wearing: “My school is super casual, but I try not to take advantage of it too much. I still want to have a difference between how I’m dressing and how the kids are dressing. I feel like my goal is usually, ‘Can I feel like I’m wearing pajamas but look like I’m wearing professional clothing?’

I think this shirt is from the Gap, and the overalls are from Aritzia. The shoes are Eileen Fisher, but via Poshmark; being a teacher, your budget’s always going to be limited. And then various jewelry that I never take off. It’s good for distracting kids who are upset; I’ll be like, ‘Do you want hear the story of my rings?’

I have one student who I adore, who is not in my class anymore but she was, and she would constantly make observations about me out loud, and sometimes she’d go, ‘Oops, I didn’t mean to say that out loud.’ I’ve also had ones be like, ‘Just so you know, you can see your bra a little bit!’”

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The Buddies

Names: Nadia Le Fleming (L) and Violet Le Noury Stewart (R)

Ages: Both girls are 7.

Where they’re headed: Both of the friends (and neighbors!) are going into second grade at different schools in Fort Greene, Brooklyn.

What they’re wearing: Nadia has to wear a uniform, but it’s pretty flexible: a bunch of T-shirts with the name of her school. And luckily her mom, Darcy, is really creative. Said Nadia, “We had so many plain shirts, and my mom wanted to make a cool one. And we had all this fabric, so she made a dress out of it! I know how to use a sewing machine, too.” Her sandals are from Payless, although Darcy said that she’ll have to wear different shoes to school, since it’s required that they be closed-toe.

Nadia is looking forward to seeing her friends and teachers, but “there’s something I’m not looking forward to: kids fighting at recess. Sometimes people take balls from each other and play too rough.”

Violet’s dress is from J.Crew, and her sandals are Saltwaters. Her mom, Leela, said that the dress is special because Violet visits Leela’s home island of Guernsey every summer and has always envied the gingham dresses the girls there wear. (“But hers is funkier!” said Leela.) Violet was still sporting temporary glitter tattoos from her last trip to Guernsey. And Violet isn’t just excited about her own outfit; she sewed clothes for her two stuffed cats, Peppermint and Biscuit, as well.

“I made their outfits!” she said. “From a flower dress and the silk under the flower dress. Sometimes they come with me [to school], and sometimes they don’t.”

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The Early Educator

Name: Emily Snedecor Knowlton

Age: 31

Where she’s headed: Into her tenth year of teaching toddlers and 2-year-olds at a school in Manhattan.

She’s extremely passionate about early education, explaining, “Ninety-eight percent of early childhood educators are women, and the pay gap between an early childhood teacher and, for instance, a university professor, or even a high school teacher, where there are many more male teachers, is huge. We’re not only dealing with the most rich age of human development, but we’re also dealing with actual genuine care and love for young children. Everybody in the field cares really deeply about young kids and their growth, and it’s kind of insane how little attention is paid. Imagine if we put the most energy — politically, financially — into early childhood care and education. Imagine what we could do.”

What she’s wearing: “I spend more time on the floor than most people, so high-waisted jeans are an absolute necessity. I need to be comfortable because at any given moment I might have to hold a small person who is crying, and my outfit is really not what’s important about that situation.

But especially with this age group, there are parents who are having their child in school for the first time ever. For many of them, first child. So I really like to feel completely myself because if I feel comfortable, I’m gonna be more confident in guiding them through tough moments in their child’s life — or the joyful moments, too. And everything has to be washable!

Levi’s are great — these are the 501 Skinnys. As a teacher, you collect a lot of really weird things in your pockets. Like, I'll come home at the end of the day, and there’ll be a piece of yarn that was a gift and a Lego that somebody was holding onto that they weren’t supposed to have. So, pants with pockets are great.

And the clogs are No. 6. They don’t make this style anymore, but they will make anything that they used to make on custom. I had admired these for years and when I finally was ready to make the investment, they no longer had them, but they were like, ‘Well, we can do it for you!’”

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Responses have been edited and condensed for clarity.

We’d love to see your (and/or your child’s) first-day-of-school outfit! Tweet at us or email alanna@racked.com, and you might be featured in an upcoming Racked post. And check out this video for a peek behind the scenes of the shoot: