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Reese Witherspoon first made her acting debut in 1991 in The Man And The Moon and earned several awards for her critically acclaimed performance. She gained worldwide recognition for her hit movies such as Cruel Intentions and Election. With the latter movie, Witherspoon earned her first Golden Globe nomination, and she has been a staple on red carpets ever since as a presenter and an award nominee. Reese, coming from her Southern roots, is known for her sweet yet powerful persona on and off the screen. Along with stylists Leslie Fermer and Petra Flannery, she has worn simple yet elegant outfits on the red carpet that make her stand out from the crowd.

From the Academy Awards and Golden Globes to the premieres of her commercially successful movies, Reese Witherspoon has always slain the red carpet with her signature outfits that give the nod to the South. Let’s take a look at some of her most expensive red carpet outfits.

2006 Academy Award

Reese Witherspoon was spotted wearing archival couture outfits on the red carpets earlier in her career with a special love for vintage outfits. The year she won the Oscar for her role as June Carter in Walk The Line, the actress wore a Dior French couture gown designed by the fashion house in 1955, as noted by New York Times. Her tulle V-neck gown shimmered with silver beaded patterns.

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2014 Oscars Vanity Fair After Party

While wearing conservative and classic dresses on the red carpet, Reese Witherspoon visibly surprised everyone with her edgy appearance and bob haircut. Even though the actress skipped the Oscars ceremony, she attended the Vanity Fair After Party dressed in a Jason Wu for Hugo Boss dress designed in silver and black with a plunging neckline.

2015 Golden Globes

Reese Witherspoon brought old Hollywood glamor to the Golden Globes red carpet when the actress arrived dressed in a silver glittering strapless gown designed by Calvin Klein, as stated by The Hollywood Reporter. She had accessorized her outfit with $1.5 million worth of jewelry by Tiffany & Co. that featured $600,000 priced diamond earrings and a platinum ring that cost $695,000.

2015 Met Gala

When Reese Witherspoon arrived at one of the biggest fashion nights of the year at the 2015 Met Gala, she went all out to style her elegant dress with hefty jewelry. She was dressed in a custom red column strapless gown by Jason Wu and Tiffany & Co. jewelry. Her diamond jewelry, including the necklace, bracelet, and ring, had a Skyscraper motif. The emerald-cut diamond earrings alone cost a whopping $122,000.

2016 Academy Awards

The actress attended her eighth Oscars ceremony as a presenter in 2016 and wore a stunning purple Oscar de la Renta gown. As mentioned by Cosmopolitan, the actress had paired her gown with accessories from her signature jewelry brand Tiffany & Co. Witherspoon, kept things simple and had styled her hair in a loose hairstyle. Her outfit became a talking point on the internet after fans noticed that comedian Tina Fey also wore a similar gown.

2017 Golden Globes

Reese Witherspoon stood out from the crowd in a sea of glittering and dark gowns in her canary yellow dress designed by Versace. The strapless gown was a part of Versace’s Spring 2017 collection, and the pastel color complemented her blonde locks and the vintage Tiffany & Co. jewelry worn by the actress.

2020 Vanity Fair Oscars After Party

While celebrities are usually spotted wearing gowns at Vanity Fair's Oscars After Party, Reese Witherspoon switched things up with an eye-popping cocktail dress. The sparkly dress was designed by Dolce & Gabbana and covered in sparkling jewels. She had matched the outfit with a simple diamond bracelet and diamond-encrusted heels.

2020 SAG Awards

Nominated for Best Ensemble Cast, Reese Witherspoon wore one of the most elegant dresses at the 2020 SAG Awards. The Celine column gown's design was black and white with a well-balanced sparkle effect and a one-shoulder necklace. Black heels and Harry Winston jewelry complimented the dress.

2020 Golden Globe Awards

Nominated for her Apple TV+ drama series The Morning Show, Reese Witherspoon dazzled at the first big red carpet event of 2020 at the Golden Globes. The actress was dressed in a custom Roland Mouret white-crepe one-shoulder gown with asymmetric sleeves. According to People, the leaf-inspired neckline of the dress complimented the Tiffany & Co. diamond pear-shaped earrings. She had completed the romantic look with Christian Louboutin's shoes.

2021 Academy Awards

Bringing the glamor back to the red carpet after COVID, Reese Witherspoon attended the Academy Award ceremony in a custom red Christian Dior gown. The dress featured a combination of red, maroon, and burgundy shades, and a black belt around the waist completed the look. The actress had completed her outfit with dazzling Bulgari jewels.

Reese Witherspoon has always dazzled the red carpet in her simple yet elegant outfits. Her style is to keep it simple and traditional, and she shows that red carpet outfits don’t always have to be over the top to stand out from the crowd. As the actress is nominated for her performance in the popular television series The Morning Show, she will be seen reigning the red carpet during the 2022 award season.

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Sources: New York Times, The Hollywood Reporter, Cosmopolitan, People