Hillary Clinton becoming President of the United States would have given daughter Chelsea Clinton the unique honor of being the First Child for a second time. Alas, that opportunity never came to fruition, but if it did, she’d have been following in the serious style footsteps of Malia and Sasha Obama (unsurprising, considering they have Michelle as their fashion role model). Over the years, Clinton No. 3 slowly but surely came into her own fashion sense, blossoming from an early loungewear enthusiast, into a woman who makes pretty solid sartorial selections. Here’s the style transformation of Chelsea Clinton, from childhood until today.
Early on, it was all about keeping it casual
When her father, Bill Clinton, was first running for his eventual seat as the 42nd POTUS, the then-12-year-old Chelsea Clinton was regularly seen sporting her go-to garbs: a simple T-shirt and denim jeans. Here, when she joined her political parents on a trip to Arkansas to await the results of his inaugural election cycle in their home state that night, she stepped off the plane wearing a loose-fitted tee with boyfriend jeans, and her no-fuss, no-muss approach to curl management was on full display. The littlest Clinton did slip in a touch of her own ethical leanings in that moment, however, because the shirt she wore displayed her enthusiasm for endangered species protection, a cause for which she’s actively worked as an adult.
When official business was afoot, she did glam it up
After Bill Clinton was announced as winner of the nation’s biggest night, Chelsea ditched her low-key digs for something a little more stately as she joined her father in accepting his new role as Commander-in-Chief, and her own as First Daughter. Not only did she tame her mane into tighter tendrils, but she also donned a classic plaid coat and gloves to match the timelessness of her parents’ own ensembles.
Growing up and into her own
As time progressed, Clinton began to adopt her own style sense. Here, when she was still just 15, she attended Easter services with her parents at Washington’s Foundry Methodist Church and looked positively ready to enroll in law school, just like her folks once did, in her smart black dress suit with complimenting collar lines on the shirt beneath.
Even her low-key travel gear got an upgrade
Here, in 1996, Clinton joined her father on the runway to board Air Force One (with Buddy the dog!) for a family getaway at Martha’s Vineyard. Not only had she found an excellent stylist to give her locks a little color punch, but she also decked herself out in casual business style with a classic grey cashmere sweater and some snappy dress pants that made her look all grown up already.
Pretty soon, she started playing with pantsuits, too
On Twitter, Hillary Clinton’s bio declares her to be a “pantsuit aficionado,” among her many other distinctions, but the former FLOTUS-turned-presidential candidate isn’t the only member of the family who’s big on trotting around in trouser combos. Here, during a trip to New Zealand for the 1999 Asia-Pacific Economic Cooperation conference, Chelsea stepped out in a blazer suit that was so akin to what her mother had been known to wear, it could’ve easily been borrowed from her closet.
She had a thing for embroidered cardigans
When Chelsea and Hillary Clinton headed to Jordan in 1999 for a meeting with its princess and to launch their lengthy European tour, Chelsea maintained her typically professional aesthetic, but her button-up sweater had just enough sewn-in ornamentation to make it just as appropriate for taking tea as it was for a meeting with royalty. Versatility is key when you’re on the move, right?
Eventually, she started to work a little more flare into her wear
In this shot from a tennis match at the 2000 Olympic Games in Sydney, Australia, Clinton was repping a lot more sass with her look than usual, including an arm-baring blouse and knee-length pencil skirt. The real kicker of the ensemble, though, was the rad pair of sunglasses she wore that made the then-student of Stanford University look like the cool college kid that she was at the time.