Over the years, Chelsea Clinton has slowly but surely come into her own fashion sense,
blossoming from an early loungewear enthusiast into a woman who makes pretty solid sartorial
selections. Here's the complete history of her style transformation, from childhood until
today.
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. 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.
After Bill Clinton was announced as winner of the election, 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 to match the timelessness
of her parents' own ensembles.
As time progressed, Chelsea Clinton began to adopt her own sense of style. 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 a collared white shirt beneath.
On Twitter, Hillary Clinton's bio declares her to be a "pantsuit aficionado," among her
many other distinctions.
"Who has the more stylish suits?"
"Oo, my mom, my mom. All those pantsuits. She definitely deserves credit."
However, the former FLOTUS-turned-presidential candidate isn't the only member of the Clinton
family who's big on trotting around in trouser combos.
During a trip to New Zealand for the 1999 Asia-Pacific Economic Cooperation conference,
Chelsea Clinton 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.
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?
While attending a tennis match at the 2000 Olympic Games in Sydney, Australia, Chelsea
Clinton repped 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.
Once Chelsea Clinton enrolled in graduate school at Oxford, she began to experiment
with a new 'do and debuted some newly-straightened and lightened locks, as seen at the 2002 premiere
of "Red Dragon". At the time, Clinton was rubbing elbows with fashion bigwigs like Donatella
Versace and pop culture icons such as Madonna, which might've inspired such a bold change
to her signature appearance. Whatever it was, though, the frizz-free look was there to stay.
Chelsea Clinton's modesty modality never went by the wayside, but she did start to cycle
in some key accoutrements to her outfits, like with a savvy neck scarf that perfectly
complemented her brown blazer during her father's 2004 speaking event at the Little Rock Arts
Center. She also earned some major snaps for subtly coordinating with her mom's similarly
earth-toned get-up at the event.
By the time Chelsea Clinton had reached her mid-twenties, her look had evolved from relatively
matronly to outright ravishing, as with the flattering skirt suit she wore to the opening
of Bill Clinton's presidential library in Arkansas in 2004. Her classically-curled coif
was the perfect fit for the scalloped collar of her pretty little blazer, and the fact
that she matched it with a nervy leather skirt for such a high-profile affair was all the
more exciting.
When Chelsea Clinton hit the trail in support of her mother's first bid for the hot seat
in 2008, she rocked a variety of jackets, but this incredible penny-colored corduroy
coat with a mandarin collar stood out for its simple splendor, and could've easily taken
attention away from the woman of the hour onstage.
Whenever she's called to the red carpet, as with her 2009 gala appearance in New York,
there's a good chance Chelsea Clinton will be showing up in a little black dress. There
are examples aplenty of her penchant for the definitive dress style, and her fresh pairing
of a tank blouse with a frilly A-line skirt and round heels is a prime example of why
we love when she opts for an LBD during a night on the town.
Chelsea Clinton has gotten professional wear down to a strict science during her time in
the spotlight, but she's also gotten a clear handle on what works for her, as evidenced
by this amazing ensemble she put together for the School of American Ballet's Winter
Ball in 2012. Her stacked, deep red necklace was just the right touch and size to give
the look the exact pop it needed, while remaining squarely within her comfort zone. Well-played
indeed.
For Hillary Clinton's second run for the Oval Office, Chelsea Clinton, then a new mom herself,
was once again busy supporting her mom's bid. For her sweet speech at the 2016 Democratic
National Convention, she took the stage in a form-fitting red Roland Mouret dress that
had the press buzzing about her trendy threads, especially since the same frock had been sported
in light pink by none other than Ivanka Trump at the Republican National Convention. Looking
back at the biggest moments of Clinton's style evolution, it's clear she's been "in" for
quite some time.
After the outcome of the 2016 presidential race, the Clintons took some time to grieve
the loss, but have since picked themselves up and seem to be doing just fine.
She emerged boldly from her family's loss in style, making appearances in bright colors
and patterns — a shift from her prior outfits, which leaned toward neutral and classic. She
grabbed our attention with the look she sported at Variety's Power of Women event in April
2017, and hasn't let go.
Straying from her bold look at the Variety's Power Of Women event in 2017, she toned it
down a bit for the April cover of the magazine. In a fitted black jacket with zipper details,
white T-shirt, and dark blue jeans, she looked laid-back, but still every bit a powerful
woman.
Variety's behind-the-scenes video interview with Clinton was similarly relaxed. Wearing
the same outfit as she did on the shoot, she kept her makeup minimal and her hair down.
Because Clinton has been wearing her hair straight for so long, you may have forgotten
how curly her hair used to be. Back in 2015, she told Elle that her curls naturally "fell
into waves" in her early 20s and admitted that she missed her ringlets.
In the past, Chelsea Clinton didn't shy away from bold patterns. While she still rocks
a colorful print here and there, you'll often see her in a solid-colored ensemble these
days. In May 2018, when Clinton attended the annual American Songbook Gala to honor HBO's
Richard Plepler, she chose a fitted forest green dress paired with nude pumps. Later
that year, Clinton attended a SiriusXM Town Hall wearing what looked to be those same
nude pumps. However, this time, she opted for a lower-cut black dress with ruffle detail
on the bodice.
When promoting her children's book "Start Now! You Can Make a Difference" on The Hallmark
Channel later in the year, she again wore a solid dress in a deep magenta color — proving
that one-color outfits are anything but boring. In 2018, SheFinds predicted that a monochromatic
style would be the biggest trend the following year. It looks like Clinton was simply ahead
of the curve.
In an interview on "The View" in April 2019, Chelsea Clinton rocked her classic nude pumps
once more, but this time she paired the heels with a similarly hued dress. Clinton, who
announced in January 2019 that she and husband Marc Mezvinsky were expecting their third
child, donned a stunning fitted blush pink dress.
Around this time, Vogue reported that a bevy of nude shades — or "50 shades of beige"
— would be one of the "most important trends of the spring 2019 season." Clinton suredly
got the memo. She even added an unexpected pop of color to the neutral color palette:
a cobalt blue cardigan — and it works!
Like many people who found themselves living a slower-paced lifestyle during the 2020 pandemic,
Chelsea Clinton adopted more relaxed fashion choices that year. Her laidback business casual
look could be seen in interviews and TV appearances carried out via video call. For example, during
a virtual appearance on "The Tonight Show" in September 2020, Clinton appeared in a simple
navy blue top.
"So, it was just like a magical time together."
The outfit seemed to be the same one she wore in an appearance on "The View" that aired
the day before, as well as one seen in a CNN appearance in August.
That's not the only outfit Clinton repeated in 2020. In March, she appeared in person
on "Story in the Public Square," wearing a floral top under a gray blazer. Clinton was
seen wearing the same top — sans blazer — months later in an appearance at the virtual
National Book Festival in September and again during a virtual appearance on "Watch What
Happens Live with Andy Cohen" the following month.
Clinton wore minimal makeup in 2020 and also adopted a relaxed hairstyle, wearing her hair
down with natural waves in all of the appearances she made from her home.
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