Inside Reese Witherspoon's Most Glam Makeup Moments

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ACADEMY AWARDS, MARCH 2002

For first trip to the Oscars, makeup artist Molly R. Stern made a statement with a “classic, timeless” look. “I went with a wonderful Delux Beauty bronzy gold shadow called Burnish Bronze [now discontinued] all around her eyes to really make them pop,” Stern says. “Paired with a pigmented berry lip, she had the flavor of an old Hollywood starlet, with all the excitement of a modern ingenue.”

02 of 12

VANITY FAIR SCREENING, AUGUST 2004

When the star stepped out with a striking new hue, Stern was “excited to work on a familiar face, with a twist!” She recalls, “Reese’s ivory skin looked even more fair with the dark hair, so we warmed up her complexion, creating a super-flushed look using blush (Stern suggests trying Laura Mercier Crème Cheek Colour in Blaze, which I dusted on the bridge of her nose as well as her cheeks, giving her a real glow.”

03 of 12

JUST LIKE HEAVEN PREMIERE, SEPTEMBER 2005

“Reese’s instinct is typically to wear more of a bright lip, but I love to see her eyes shine,” Stern says. “Reese is so wonderful to work with because she is so trusting and lets me pick out the colors. For this look, because her headband was her main accessory, she agreed with me that a neutral hue was the way to go. So we did a dusty, smoky eye using Nars Ashes to Ashes, and kept the lips looking more nude and natural.”

04 of 12

WALK THE LINE PREMIERE, NOVEMBER 2005

Even matching her lipstick to her dress is no sweat for the actress. “She has an amazing confidence,” says Stern, recalling, “I custom blended lip colors to perfectly match Reese s dress. I brought my entire kit along so that we could create the perfect color! It worked because the rest of the look is clean and bright.”

05 of 12

ACADEMY AWARDS, MARCH 2006

“This is one of my favorite looks for Reese, she just looks simply beautiful,” says Stern of that year’s Oscar winner (for her role in Walk the Line). “To create the look, we turned to the gown for inspiration, and tried to pick up on the tones in it, and her accessories. I used Jurlique Rosewater Balancing Mist to invigorate her skin. I also used a soft gray shadow on her lids and kept the lip rich, yet soft and peachy. To me, this is an iconic Hollywood starlet.”

06 of 12

GOLDEN GLOBES, JANUARY 2007

Yes, that electrifying yellow Nina Ricci dress was everything, but Reese’s bangs reveal will go down as one of the biggest beauty moments of awards season history. “Mark Townsend cut her bangs while we were getting her ready!” Stern shares. Then, Stern swept NARS Blondie eyeshadow on her lids and the hollows of her cheeks to create a subtly sexy makeup look. “It was different than we had ever seen Reese. There was something more mature and sexier about her look.”

07 of 12

VANITY FAIR OSCAR PARTY, FEBRUARY 2009

“We wanted to choose a blue color that complemented her gown and eyes – without it being too match-y – and smudged it with black kohl liner from the [now discontinued] Jillian Dempsey for Avon Professional collection. It s rich but super blendable, so it was the ideal addition to create the perfect drippy smokey eye,” says Stern.

08 of 12

MONSTERS VS. ALIENS PREMIERE, MARCH 2009

If Reese’s makeup looks out of this world, it’s because Stern wanted to create “a more post-apocalyptic look.” She says, “we used the dress as our muse for this look – playing off of the metallics. I loved how the dress gave a body armor type look, so I didn t want to have anything too hard or harsh on her face. No bold eyes or lip. I used an Avon mascara in brown – not black – to soften the look.”

09 of 12

GOLDEN GLOBES, JANUARY 2012

“I love how bright Reese’s complexion is and how just the subtle line of the eye adds a gorgeous element of va-va-voom,” says Stern, who used a black cream liner on the upper lash line, while keeping the lower lash line clean. “I wanted to show that you don t need a lot for the makeup to look sexy. For me, less is more.”

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WILD SCREENING, OCTOBER 2014

Did you go wild upon seeing Stern tease this look on Instagram, too? When the star revealed an all-over bold look, it was because “something about the dress reminded me of a female bull fighter, it yelled, ‘come and get me,’ and I needed to give her a makeup look that was just as powerful,” explains Stern. “The key was balancing the elements so they didn t look too extreme or dark. I used matte shadows and Clinique High Impact Extreme Volume Mascara so her eyes really dazzled. I also added a bit of contouring and an extra pop with a bright lip.”

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GOLDEN GLOBES, JANUARY 2015

“Here, it was all about glistening skin and eyes,” says Stern. “I was inspired by Reese’s work in as an actress and producer of Wild, which is why [I wanted her to] shine like the prize she is.” Creating a look that complemented the star’s Calvin Klein Collection gown, Stern focused on flawless skin. “I used Laura Mercier Silk Cr me Moisturizing Photo Edition Foundation [Editor’s Note: mark your calendars, this hits shelves in April], which made it very easy.”

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SAG AWARDS, JANUARY 2015

Channeling an “old Hollywood” feel isn’t something Stern and the star often do, but when the vibe inspired Stern, she reached for rich, dark colors. “I used Laura Mercier Paint Wash Lip Colour in Orchid Pink and layered it with Vermillion Red to give an added punch. But, the key to this look was actually a rich matte eye – I actually used blush (Laura Mercier Cream Blush in Blaze), which let me build a strong bordeaux base with a deep and enriched finish.”