Dressing for the Drop-Off: From a Lounge Set to a Luxe Cardigan

I’ve long felt like strutting up to school drop-off in Brooklyn can feel a bit like a runway. Yes, the accessories are less cool (I’m typically toting my kid’s backpack on his behalf), but the pressure to put some effort in for spontaneous interactions with other parents is real. And while it’s tempting to neglect myself in the morning as I race to get both kids out the door, I’ll admit that taking a moment to consider my style is one of the best ways to set my day off on the right note, especially as a mom who primarily works from home.

That said, winter is hard. This month saw temps dipping well below zero (not counting the real feel), and it goes without saying that layers are required. While it’s true that my sartorial decisions this season could pretty much stay out of sight beneath my puffer coat, it’s the unexpected detour to the local coffee shop, the long-scheduled classroom concert, even a simple lost-and-found drive-by that make it a given that what I wear will be on display at some point.

Here is what I wore this month to make sure I not only felt practical and polished, but also warm.

A button-down feels like old faithful in my closet, but the frigid temps had me leaning on an additional layer: this chic ribbed turtleneck from Everlane. Madewell’s “easy” shirt is exactly that—easy—so, after giving it a quick steam (alongside my kid’s jeans that had been crumpled up in his bottom drawer), I felt good to go. But that’s not all: I paired it with a colorful neck scarf (dopamine dressing always wins in winter, IMO) and a beloved pair of petite-friendly Frame jeans.  

If you want a work-around for a colder morning, merino wool is the way to go. Honestly, this popcorn polo cardigan from Misha & Puff is so warm that you almost don’t need a coat. I also love the soft rose hue and detailing. I got so many compliments on this statement style as I approached the drop-off line. I kept the look simple with blue jeans, worn over opaque red tights (my version of long underwear on this frigid day). My Margaux loafers (and their robust treads) completed the look.

Like I mentioned, my son had the cutest-ever concert this month (given the state of the world, it was superhero-themed). This felt like the perfect moment to wear a Clare V sweatshirt with a message: “Vive le resistance,” it read. I wore it with a pair of MOTHER denim (their petite line is the best) and a delicate tennis necklace, too. Like I said, layering is the style throughway this season, so I also kept a blazer on hand to throw on over my shoulders just in case the auditorium felt extra chilly.

I mostly work from home, but on the days that I do commute to the city, I typically take on drop-off for my son en route to the train. To be clear, I would never do the mile-long walk to my son’s school in heels—instead, I swapped my sneakers for heels upon arrival at the office—but this particular pair from Inez somehow keeps me blister-free, no matter the paces I put them through. Still, this cashmere cardigan from White & Warren is my outfit’s centerpiece, delivering a subtle dose of prep while keeping me cozy and ready for the season’s fluctuating temps. Paired with a cargo pant from Scanlan Theodore, this is an outfit that felt polished for school drop-off and in-person meetings.

To get my kid to school, we walk a mile—and in moments of desperation, i.e. like this morning when teeth brushing and lunch box-packing took a little too long, we take a cab. But I still wanted a look that left me warm and feeling pulled together. This lounge set from AYR (aptly named the Bodega Run) in a pretty and light purple-y hue gave me the pop of color I needed while helping me stay cozy. With my Veja sneakers and a wool topper (from Rudsak, similar here), it felt functional, but most importantly like effort was made.