Who Cares What I Wear at School Drop-Off? Me.

“New York Woman” — three small words that tell a big story.

A story I hoped to embody, but might never get the chance. The words were embroidered on a T-shirt I saw at Out of the Closet, the secondhand store in the Boerum Hill neighborhood in Brooklyn last week but opted not to buy simply because I ran out of steam, and now, I regret everything.

Retracing my steps, I rummage through the rack. Someone else beat me to it. Probably another local mother. Maybe Maggie Gyllenhaal.

And so it goes, as I schlep up and down Atlantic Avenue in early September ahead of my kids’ Sept. 8 return date, looking for little gems to enhance what I like to call my “drop-off outfits.” You know, the clothes one wears when we take our kids to school. A tradition that is distinctly — though certainly not exclusively — New York.

Obviously, the art of the drop-off outfit is to look like you do not care about the drop-off outfit. However, I’m not ashamed to admit that I do put some consideration into the fashion of it all, especially during the tour de force that is the first two weeks of the school year. There are so many transitions to navigate, so many forms to be filled out, so many seaweed snacks to dispense.

For those of us who get excited by style, it can’t hurt to feel some sense of chic along the way. Of course, there are way more important things in parental life than metallic Tevas and Mansur Gavriel, but for me, with two young children in different schools, a partner who is often away, and a full-time job that can feel all-consuming, if a stupid bougie, tie-dye sweatsuit is going to help me endure, then bring on the Aviator Nation. Also, I work from home, which is a wonderful thing, as professionalism and I have issues.

Clockwise from top left: Humera Baburi, wearing Zara; Tamzin Baker (left, with baby) and Sara Whitmore; Dominique Massey in an Old Navy unitard and Gucci fanny pack; Alexis Bittar in a Marine Layer tee, Steven Alan shorts and vintage Nike Air Jordans. Credit…Ali Cherkis for The New York Times

My children go to public school, but we live in Brooklyn Heights where there are several private schools, many celebrity parents (Matt Damon, Emily Blunt, Keri Russell, etc.) and swarms of families who can afford gorgeous wardrobes. Every morning I see a runway of Rachel Comey jumpsuits, Suzie Kondi puff sleeves and Anine Bing basics.

Just today, I passed the popular post-drop-off hangout, a cafe called Maman, and moaned to myself, “It’s like Ulla Johnson on drugs in there!” Mind you, I say this out of love and jealousy. I may roll my eyes at the radiant mom wearing a $695 LoveShackFancy dress, but make no mistake: I want that dress. I can’t tell you the evil things I would do for a pair of those furry, slip-on Gucci loafers that the really rich moms wear.

Still, none of that is the look I’m personally striving for (or could ever afford) at drop-off.

For starters, I want my outsides to match my insides. I’m talking about struggle. Attitude. The look needs to land somewhere between “My Kids Are My Life” and “Kill Me Now.” It needs to exude that I’m a scrappy, unmarried, mildly unhinged mom who is constantly hustling and hitting the gas, and, yes, I might look terrible, but I have taste.

This translates to heavenly T-shirts, bulky sweatshirts, the good ol’ mom jean and a rotation of leather jackets and trench coats that were once expensive, but less so at Nordstrom Rack. For this year’s drop-offs, I added checkered pants by MOTHER and a gray Champion sweatshirt that reads “MoMA.” (Have I been to MoMA in the last decade? Nope, I have not.)

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I also splurged on a black Zadig & Voltaire bag because it was aggressively studded, and a little punk works well against all the shmattes. I agonized over a gold fanny pack from Rachel Comey, which cost $425, but in mom math that is one semester of hip-hop at Mark Morris, so I moved on. Instead, I got a much cheaper, neon-yellow “belt bag” from Shinola.

Clockwise from top left: Jessica Flynn, wearing vintage; Jona Brisske, wearing Varley Long; Krissy Harris, wearing a shirt from State Bicycle Company and Adidas shoes; Raquel Balsam, wearing Sea.Credit…Ali Cherkis for The New York Times

Trust me, I get it. Most normal, happy, well-adjusted parents wear Old Navy, or Everlane, or whatever is clean and available. Alison Ratner Mayer, a 42-year-old child therapist in Framingham, Mass., told me, “I’m either wearing very typical work clothes, or if I’m not going to work, I wear whatever is acceptable to leave the house in, and smells fresh.”

Even at my kids’ schools, it’s not some “scene”; almost no one is looking. The vast majority of my mom-friends and mothers at-large are not thinking (at least not as enthusiastically) about this stuff. But some of us are. I’ve always loved great clothes. I was raised on tag sales and T.J. Maxx, and the emphasis was always on great clothes.

Last year, I realized that I complimented other parents’ outfits and accessories a little too much. It made me seem superficial, when in reality I was just too burnt-out to talk about anything deeper than Dôen and Sézane. Deliberately, I don’t do that anymore. (Except for right now, I guess.) The point is, I still remember whose style I admired.

Catherine Meagher, 40, a senior manager at Phaidon, is one of those moms who always caught my eye. “It’s all determined by my work day. If I’m going into the office after drop-off, I am typically dressed professionally, but true to myself,” she told me. “A combination of structured menswear-inspired foundation pieces with femme details like volume, bows, ruffles and floral prints.” She added: “The one consistent is comfortable.”

My sister, Rachel Karasik, who’s 42 and a small-business owner in Brooklyn, has a popular Poshmark closet, Hunt and Sage, that has a large clientele of budget-conscious moms. When I asked her if the “drop-off outfit” is something her shoppers think about, she said, “Definitely. Especially in the fall. All parents are worried about first impressions — it’s human nature.”

I have one mom friend, Raquel Balsam, a 36-year-old TV producer, whom I met at drop-off years ago, and whom I befriended exclusively because I liked her style. When I confessed this to her over the phone recently, she responded, “Really? It’s called, ‘What can I add to my pajamas that tells the world I’ve somewhat got my life together.’”

Clockwise from top left: Annette Fodero, wearing Hill House Home; Casey Kahn, wearing a Dôen dress and Marlow Goods bag; José Rolón, a.k.a. @nycgaydad on TikTok; Dino Delvaille, wearing Scotch & Soda and Louis Vuitton

I’ve also noticed a few dads with drop-off swagger. I checked in with two of them about their approach. Kenneth Ebie, 43, executive director of Black Entrepreneurs NYC and founder of Ebie Strategies, said his presentation is rooted in something deeper as a Black father: “I’m always aware that how I show up in the school community impacts how my kids are perceived and ultimately how they’re treated. So whatever I do, my look has got to be clean. Raggedy is never an option.”

On the other hand, Joost Heijmenberg, a 46-year-old photographer, said, “Sorry, no. I do not have a drop-off style.” Alas.

As I continue to shop and thrift, how do I decide what makes the final cut? Easy. I imagine bumping into Ethan Hawke on the street — which does in fact happen, per my earlier point. Then I ask myself if I’ll feel cool enough when our paths cross. What would Ethan Hawke think?

There is one woman in my building whose style is everything mine is not, which is: truly effortless. Emy Consula, 39, a nursing student and mother of two, has a hip, grunge-y drop-off style that I can only describe as Kurt Cobain as a Brooklyn mom (and not dead).

In the elevator, when I asked her what her fashion philosophy was, she looked at me like I had officially lost my mind. “Something like Urban Outfitters meets Alexander Wang, right?” I asked, totally serious. When Emy realized I wasn’t joking, she indulged me. “It’s a capsule collection of chaotic, exhausted and who cares?”

Suffice to say: I found my New York Woman.

Alyssa Shelasky is a freelance writer in Brooklyn Heights. Her latest book, “This Might Be Too Personal: And Other Intimate Stories,” came out in May.

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