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Shailene Woodley chooses her moments to make heads turn at the red carpet. The actress was known for her supporting roles in acclaimed movies and came to prominence in 2014 with the coming-of-age romance drama The Fault In Our Stars. The movie catapulted her into stardom, and she became a staple personality at red carpet events. Since her first red carpet appearance, Woodley had a background in various fashion houses, which helped her make smart choices for her outfits. Over the years, she has worked with various stylists, including Ilaria Urbinati, Kris Zero, and Rachael Wang, who have helped shape her style into bold yet minimalist looks.

Picking comfort over style, Shailene Woodley is also known to walk the red carpet barefoot when the heels create a hassle. From wearing extravagant Valentino gowns to showing her refreshing style in Louis Vuitton, let’s take a look at her most expensive red carpet looks.

2014 Met Gala

The theme of the 2014 Met Gala was Charles James: Beyond Fashion, and the actress made heads turn on her appearance at the star-studded event. Woodley was dressed in a Rodarte off-the-shoulder gown from the fashion house’s Fall 2014 collection. The highly decorative look got completed with metallic embellishments and sheer chiffon details. She had styled her hair in an edgy pixie hairdo and smokey eye makeup look.

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2018 Met Gala

Shailene pulled off the 2018 Met Gala theme of Heavenly Bodies: Fashion and the Catholic Imagination with her look. The actress paid homage to Joan of Arc with her custom Ralph Lauren dress in metallic, who is a religious figure, as noted by PopSugar. It reflected her fierce personality with the armor-like look with the turtleneck and over-the-knee black boots.

New Bond Street Maison in 2019

In 2019, Louis Vuitton reopened the New Bond Street Maison in London and threw a lavish cocktail party with many A-list celebrities as guests. Dressed in Louis Vuitton, Woodley showed her eccentric style with a long puff-sleeved blouse detailed with a leopard print and a black and yellow checkered leather skirt. She brought a mini purse matching the skirt pattern with a pair of black boots.

2019 Fashion Awards

Shailene Woodley became the most talked-about celebrity when she arrived at the 2019 Fashion Awards dressed in an extravagant puffer skirt. According to Vogue, she was dressed in a navy blue quilted skirt from the collaboration between Pierpaolo Piccioli and Moncler. Designed in the hues of blue, it was a hybrid gown and jacket.

2020 Golden Globe Awards

The actress has been keen on wearing racier outfits in the last few years, and she showed her daring side with a custom Balmain gown which is one of her edgiest looks of all time. The sequined black and blue gown had a side slit and a circle motif that highlighted the dress. She had completed the outfit with Balmain heels and Bvlgari sapphire and diamond earrings, rings, and a coiled diamond bracelet.

2014 Divergent German Premiere

One of her big red carpet events, Shailene, served stunning looks during the Divergent press tour alongside her castmates. One of her most memorable outfits was from the Germany Premiere when she wore a white Zuhair Murad from the Pre-Fall 2014 collection. The gown featured a plunging neckline, bold shoulders, and a structured silhouette enhanced by the gold metallic embellishments.

2018 Golden Globes

In the era of #MeToo and #TimesUp, the 2018 Golden Globes saw celebrities standing in solidarity and wearing black to fight sexual misconduct in Hollywood. Woodley stood up for the moment, proudly dressed in a two-tone black and white Ralph Lauren gown from the Fall 2017 collection. She had completed her look with a metallic belt on the ballgown-style dress.

2012 Academy Awards

At her first appearance at the Academy Awards, Shailene Woodley wore an effortlessly chic white Valentino gown. White was one of the most popular colors of the night, and her long-sleeved couture outfit was a head-turner, as reported by Huffington Post. Pulling her hair back in a bun, she had her signature smoky-eye look to compliment the outfit.

2019 Cannes Film Festival

Shailene Woodley attended the Rocketman screening at the 2019 Cannes Film Festival in a Christian Dior Haute Couture from the 2019 collection. She was dressed in a shirt and shorts with a satin-lapeled black cashmere coat over it, and the only jewelry Woodley wore was a pair of Plume de Paon pendant earrings by Boucheron.

2017 Emmy Awards

Nominated for her role in Big Little Lies, the 2017 Emmy Awards was an exciting night for the actress. As mentioned by The Hollywood Reporter, she was dressed in a custom emerald green gown designed by the fashion house Ralph Lauren. The outfit featured a small train and a plunging neckline. Woodley also debuted her loosely tied blonde locks with the look.

Shailene Woodley has always worn memorable outfits on the red carpet, from movie premieres to award shows. Never afraid to show her laid-back personality with the gowns, Woodley is always unapologetically herself. The actress was last seen in the Netflix romance movie The Last Letter From Your Lover in July 2021.

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Sources: PopSugar, Vogue, Huffington Post, The Hollywood Reporter