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25 of Reese Witherspoon's best looks

Want to dress like a Hollywood star? Reese Witherspoon's best looks are a great place to start

If you're keen to add star quality to your outfits, then Reese Witherspoon's best looks are the perfect place to start for a style refresh. The actress has frequently put her most fashionable foot forward.

Witherspoon first found fame with her breakthrough role in the 1999 film Cruel Intentions. She then went on to solidify her position as one of Hollywood's biggest stars appearing in Legally Blonde, Wild, American Psycho and Walk The Line - the latter of which saw her pick up a Best Actress award at the Oscars. She also more starred in the hit TV series The Morning Show and Big Little Lies.

The A-list mother-of-three - who has a son and daughter with ex-husband Ryan Phillippe, and another son with ex-husband Jim Toth - has additionally increasingly made a name for herself behind the camera. Her production company, Hello Sunshine, has released hits including Where the Crawdads Sing, Daisy Jones & The Six and Little Fires Everywhere.

As befitting such a stellar on-screen career, Witherspoon frequently wows at glamorous awards ceremonies and movie premieres and is a fan of both bold colours and serious sparkle. However, the star also impresses off the red carpet too, with her impeccable dress sense extending to chic daytime looks that feature classic staples and cosy knitwear. We're certainly inspired...

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The glittering vintage gown

An early adopter of sustainable fashion, Witherspoon wowed in a Dior dress dating back to 1957 at the Oscars ceremony in Los Angeles in 2006. The star wore a sparkly gown, featuring a plunging neckline, to pick up the Best Actress award for her role in Walk The Line. She finished off the glamorous vintage ensemble with an elegant updo and a pair of diamond earrings.

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The navy peplum-hem dress

Witherspoon meant business when she stepped out in New York in 2022 in a navy mididress. The off-shoulder frock, which featured a chic peplum hem, makes perfect office attire. She finished off the sharp ensemble with an oversized black belt and black court shoes.

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The button-down LBD

There's nothing quite like an LBD - meaning 'little black dress' - when you're heading to a party. Witherspoon exuded serious style in a sleeveless Schiaparelli frock, featuring elegant gold buttons from neckline to hem, at the Los Angeles premiere of Daisy Jones & The Six in 2023. She paired it with a sleek ponytail and black heels.

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The yellow cocktail dress

Witherspoon made her first appearance following her divorce from her first husband and Cruel Intentions co-star, Ryan Phillippe, at the Golden Globe Awards in Beverly Hills in 2007. Her shimmery sleeveless yellow cocktail dress, by Nina Ricci, is now described as one of the best 'revenge' dresses in fashion history. She paired it with sleek blonde locks and red satin heels.

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The sweater and jeans combo

While she might be one of the biggest A-listers, Witherspoon has shown that she's also a fan of dressing down like the rest of us. The star was pictured out and about in Los Angeles in 2009 in a navy v-neck sweater and classic straight-leg blue jeans. She finished off the laid-back ensemble with black sunglasses, layered gold jewellery and a pair of white Vega sneakers.

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The yellow thigh-split gown

Witherspoon wore another take on the 'revenge' cocktail dress in this yellow frock on the Golden Globe Awards red carpet in 2017. This time, her Versace floor-length gown featured a plunging neckline and subtle thigh split. She kept things elegant with a sweeping fringe and a statement necklace.

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The cardigan and jeans combo

Witherspoon provided a clever lesson on how to dress up a cosy cardigan while stepping out in Los Angeles in 2018. The lightweight navy knit, featuring chic pearl buttons, was paired by the star with blue straight-leg jeans and heels in black. She finished off the elevated daytime ensemble with a pair of black classic sunglasses.

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The sparkly check minidress

Witherspoon is proof that there's no age limit to looking great in a minidress. The star, at the time aged 45, wowed in a longsleeved sparkly number from Carolina Herrera, that featured a fun pink and red gingham design, at the premiere of Sing 2 in Los Angeles in 2021. She finished off the ensemble with wavy blonde locks and a pair of bright red heels.

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The blouse and jeans combo

Witherspoon exuded laid-back cool at one Hollywood event in the 1990s. She tucked a cream button-through, long-sleeved blouse into a pair of classic blue straight-leg jeans, which were cinched in with a black belt that matched her small cross-body bag. The actress, then a rising star, also wore minimal dewy make-up.

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The sparkly blue dress

Witherspoon looked every bit the leading lady at the Emmy Awards in Los Angeles in 2022. The star sparkled in a sleeveless navy sequinned dress by Armani Privé that featured a subtle high-low hem. She accessorized with a statement aquamarine neckline as well as a pair of strappy heels.

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The knee-high black boots

As a budding actress in her late teens and early 20s, Witherspoon was already displaying serious fashion know-how. She wowed in a strappy black dress, with a plunging neckline, at one red carpet event in the 1990s. However, it was her footwear that really elevated the look - she teamed the frock with a pair of classic knee-high black boots and bare legs for the smart evening do.

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The red pant suit

While she tends to favour dresses, Witherspoon stepped out in a striking red pantsuit for a photocall for The Morning Show in Beverly Hills in 2021. The custom red blazer, worn over a black top, and matching boot-cut trousers - which featured eye-catching yellow and black stripes - was created by celebrity tailor Rich Fresh. She accessorized with gold hoop earrings and a pair of black heels.

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The denim jacket and dress combo

Witherspoon, just like us, understands the power of the denim jacket - which is essential to any capsule wardrobe. The star threw one over a sweet blue and white gingham summer dress for a day out in Los Angeles in 2017. She accessorized the stylish look with a pair of blue sunglasses, a straw bag and tan-brown platform heels.

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The silver cocktail dress

Never one to shy away from a sparkly dress, Witherspoon stunned at the Vanity Fair Oscar Party in Beverly Hills in 2020. Her white and silver Dolce and Gabbana frock featured a square neckline and hem that fell elegantly just below the knee. She finished off the glamorous ensemble with a bright pink lip and a pair of silver strappy heels.

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The fuchsia pink midi dress

One of Witherspoon's most iconic roles was as Elle Woods in Legally Blonde. She channeled the character in a fuchsia pink midi dress, by Emilia Wickstead, at the Where The Crawdads Sing premiere in New York in 2022. The star paired the Barbiecore frock - which featured a scoop neckline and ruched detailing at the waist - with a pair of metallic strappy heels and wavy blonde locks.

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The off-shoulder green gown

Witherspoon brought serious glamour to the red carpet of the SAG Awards in Los Angeles in 2018. Her dark green off-shoulder gown was by Zac Posen and featured a subtle geometric design. The star kept the rest of her look simple, with an elegant smokey eye, emerald drop-down earrings and her tousled locks swept to one side.

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The blue pantsuit

It's not all about girly dresses for Witherspoon. The star likes to mix things up from time to time with a pantsuit, just like the bold blue look she wore out in New York in 2022. She paired the tailored ensemble with a blouse in a lighter shade and navy court shoes and finished off the look with her long hair styled wavy.

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The hot pink gown

Witherspoon took inspiration from classic Hollywood with her outfit for the Met Gala in New York in 2014. The star opted for a strapless hot pink gown by Stella McCartney, featuring an elegant sweetheart neckline and small train. She channelled fellow Hollywood leading lady, the late Marilyn Monroe, with her sleek blonde bob and finished off her look with a pair of diamond earrings.

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The blue peplum dress

We love the girly style, and Witherspoon is arguably the queen of dressing this way. The actress wore a baby blue sleeveless dress by Valentino to the premiere of Netflix's Your Place Or Mine in Los Angeles in 2023 - which featured an eye-catching peplum-style waist. She finished off the look with a pair of black strappy heels and discreet jewellery.

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The red halterneck gown

Red is one of Witherspoon's go-to shades - and for good reason. The star wowed in a striking halterneck gown, from Christian Dior, at the Oscars in Los Angeles in 2021. The dress featured elegant pleating and was cinched in at the waist with a skinny black belt. She finished off the head-turning ensemble with diamond earrings and smokey eye make-up.

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The 1980s-style gown

In a departure from her usual ultra-feminine style, Witherspoon played around with 1980's glamour at the Met Gala in New York in 2017. Her navy and black Thierry Mugler one-sleeved look featured an exaggerated shoulder and subtle thigh split. She wore her hair in a dramatic up-do and slipped on a pair of black platform heels.

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The denim jacket and maxidress combo

While we may be most accustomed to seeing Witherspoon grace the red carpet in sweeping gowns, she is also often spotted out running errands in laid-back wardrobe staples. The star looked stylish in a black maxidress featuring multicoloured polka dots, with a dark blue denim jacket thrown over the top, while out in New York in 2022.

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The navy thigh-split dress

Witherspoon shimmered her way into the InStyle Awards in Los Angeles in 2021. Her navy Michael Kors dress featured a sparkly finish, along with cut-out detailing and a small thigh split at the side. She kept her blonde locks sleek and straight and finished off the ensemble with a pair of navy platform heels.

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The off-shoulder floral minidress

There are few things as stylish as an off-shoulder neckline - as demonstrated by Witherspoon's Victoria Beckham mini dress at the Sing premiere in Toronto in 2016. The pink form-fitting frock also featured a subtle floral design, and she paired the look with tousled waves and a pair of ultra-high heels.

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The white one-shoulder gown

At the Golden Globe Awards in 2020, Witherspoon was nominated for her role in The Morning Show. For such an important occasion, the star stepped out in a dramatic one-shouldered white gown by Roland Mouret, which featured an elegant gathering at the waist. She finished off the look with a slicked-back bob, smokey eye make-up and diamond earrings.

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Want to dress like a Hollywood star? Reese Witherspoon's best looks are a great place to start