Over the past three decades, parenting trends have shifted from authoritarian to permissive—and ultimately, to what we now call “gentle.” Mothers and fathers have traded in Dr. Spock for Dr. Becky, and allowed the great Emily Oster to calm our neuroses about eating a little sashimi in our second trimester (so long as it’s from the “good” Japanese restaurant).
Yet, while the rules of child-rearing is an ever-changing sport, great mom style (aka your school drop-off look) hasn’t really changed—and that’s a good thing. What reads as cool mom is surprisingly similar today as it was when Goldie Hawn was pushing a newborn Kate Hudson in an umbrella stroller. Then and today, the formula for looking good whilst with a toddler remains pretty much the same: comfortable, somewhat minimalist classics that are well accessorized, usually with a perfect pair of black sunglasses and a luxe-meets-utilitarian bag. It’s a look that screams, “I’m going to the park. And guess what? I didn’t forget the snacks.”
While Instagram sees mom style as a marketing ploy of getting you to purchase yet another barn coat or kick-flare pant, might we suggest turning your gaze to some throwback mom inspirations (as well as some new additions to the mom club) for a little guidance? Sure, it’s not the red carpet, it’s preschool drop-off—but feeling good at 7:45 am after being berated by a two-year-old for burning a waffle requires a bit of finesse. Ahead, from Meg Ryan and Whitney Houston to Jennifer Lawrence and Sarah Jessica Parker, take a look at the celebrity moms who make mom-ing look good.
Cindy Crawford
You could argue Cindy Crawford, seen here in 2001 with son Presley, is the GOAT of perfect mom style—and you wouldn’t be wrong. Her combination of straight leg jeans, flat boots, and a deep red turtleneck sweater is still timeless more than 20 years later.
Claudia Schiffer
Claudia Schiffer proves the power a simple silk scarf has in elevating an ensemble—even when rushing out the door with a coffee mug still in hand.
Whitney Houston
Right up there with school drop-off, the mom airport look is a puzzle in its own right. You’re preparing for a thankless day of battle after all. In 1995, Whitney Houston made schlepping look easy carrying daughter Bobbi Kristina along with a pack of water bottles in an oversized blazer, light-wash jeans, Chuck Taylors, and a Fila visor.
Gwyneth Paltrow, 2005
Some pieces just never go out of style. See: Gwyneth Paltrow wearing the classic North Face puffer coat in 2005—the most practical mom staple then and now.
Yoko Ono
Between Yoko Ono’s face shield sunglasses and Sean Ono Lennon’s aviator jacket, the stylish mother-son duo, seen here in 1983, were very much setting the pace for future trends to come.
Sofia Coppola
A striped Charvet shirt is one of Coppola’s wardrobe staples as she often wears them when directing her films. But the simple button-down look, seen here in 2011, is equally chic for play date-duty.
Goldie Hawn
In January 1989, Goldie Hawn and Kurt Russell made the case for coordinating in statement outerwear. Sure, the acid wash jeans skew a bit dated—but Hawn’s oversized shearling leather bomber jacket reads very now. In fact, how about this one from Toteme?
Diana Ross
Diana Ross, as seen here leaving Cedars Sinai Medical Hospital after giving birth to her third daughter, delivered quite a strong sartorial kickoff into motherhood in oversized shades and an easy black turtleneck.
Sarah Jessica Parker
In 2012, Sarah Jessica Parker was the picture-perfect autumn mom in a casual sweater coat, vintage t-shirt, and classic Converse.
Meg Ryan
Meg Ryan was equal parts cozy and grunge color-coordinating with her son in 1992. Consider her hiking boots a precursor to the gorpcore trend as we know it today and a reason to add these Prada lace-ups to your wishlist.
Princess Diana
Princess Diana’s tiny gold watch and simple hoop earrings are the ideal accessories for chic, hands-on moms.
Cindy Crawford
The supermodel makes baby-wearing look easy in an oversized cream turtleneck, tortoiseshell sunglasses and a Baby Bjorn.
Beyoncé
A black knit beanie can be a godsend for new moms strapped for time. Here, Beyoncé with Blue Ivy in 2012, paired hers with an oversized, navy parka for an easy, utilitarian look.
Jennifer Lawrence, 2023
Jennifer Lawrence proves you can’t go wrong with the classics—a bright red hoodie, black overcoat, and Adidas Sambas for chasing after a toddler.
Sarah Jessica Parker
Sarah Jessica Parker, seen here in 2005, makes a case for pulling out all your old Y2K favorites—namely the Balenciaga City bag and UGG boots.
Princess Diana
Nothing screams classic sporty mom more than a Ralph Lauren polo sweater and a great blow out. This should do the trick for the former.
Sienna Miller
Sienna Miller matches with her daughter in white sneakers and tailored denim in 2016, for a great mommy-and-me moment.
Jennifer Lawrence
A good styling hack for dealing with the primary school years: Opt for primary-colored knits.