As a former California girl whose mom could have easily gotten away with wearing pajamas to drop me off in the school car pool lane since she never exited the vehicle, my current routine of walking my kids to their school on the Upper East Side every morning was, at first, quite the foreign concept. Not only is there the walking itself (think sensible footwear, which definitely does not include house slippers), but there's also the social aspect of seeing fellow parents every morning and wanting to put your best foot forward fashion-wise. Sometimes, that entails polishing up my workout clothes for my post-drop-off Pilates class, and on other days, I'm dressing for meetings, press previews, and lunches straight after I leave the school. Luckily, I'm greeted with all the inspiration I need every day from the fellow moms in my neighborhood.
Walking down the street can, at times, feel like scrolling through a carefully curated social feed, and for all of our benefit, I take notes! Today, I'm spilling the tea on the seemingly simple items I see every mom wearing in order to master chic, comfortable, and cool drop-off style. From suede slides (ranging from Ugg to The Row) to baseball caps for rain or bad hair days, these are the pieces I'm keeping at arm's reach for easy outfits every day. To see everything that made the cut accompanied by selfies of some of my own early morning outfits—you might even spy my sons' backpacks on my shoulder in some!—simply keep scrolling.
This can be anything from a classic Barbour barn jacket to an elevated Toteme style to something from Alex Mill—a big UES favorite. Just make sure it's slightly oversize and has sufficient pockets for everything you're juggling. Bonus points for a contrast collar.
Whether you're team Ugg, The Row, or somewhere in between, minimalist suede slides are a footwear must pretty much year-round, but they're especially fitting in fall. I style mine with jeans, leggings, silky pants, and more, and they are a lifesaver for mornings when I'm literally running out the door.
When I tell you that I lived in my poplin and taffeta cargo pants all spring and summer, I truly mean it—as did pretty much all my mom friends. While I'll be holding on to those for as long as I can as we get into fall, I've already found a few heavier-weight replacements for colder weather, starting with the Reformation pair you'll see below.
Whether it's raining, freezing, or simply a bad hair day, a classic-fitting baseball cap will not only serve a purpose in your outfit, but it can also tie it all together. Anything will work—from Celine styles to nondescript, plain ones (my go-tos are my husband's vintage sports caps—regardless of your budget.
Call it the Miu Miu effect, but there's something about a polo-neck top that looks cute and always gives put-together, and the UES moms have taken note. Aside from some essentials such as leggings, sneakers, and oversize Chanel bags—kidding but also not—it's probably the item I spot the most when I'm walking around my neighborhood and at the school.
This bag is a must for both function and style. Everyone knows big bags are trending, but they've never not been trending in the mom world. We are constantly toting a ton, and an It bag in suede or leather is the ideal way to do it in style.
My current trick for dressing my leggings up is a sleek, long coat and flats. In the winter, that will transition to boots, a heavier jacket, and plenty of layered knits. Regardless of how you style them, you will need a quality pair that, even after endless washes, won't look like they've been through the wringer.
You know the low-cut, minimalist, and retro-inspired sneakers that are probably the closest thing you can get to ballet flats with laces? Yeah, they're everywhere, including in my own closet in multiples. They work so well with pants because they don't create scrunching or a bulky look, making them incredibly useful and easy to style.
