Tessa Thompson's Incredible Style Moments Over The Years

Tessa Thompson has long been one of Hollywood’s most fearless fashion risk-takers. Whether she’s commanding the red carpet in avant-garde couture or redefining street style with unexpected silhouettes, the actress consistently uses fashion as a form of self-expression. Never confined to trends, Tessa, now 42, gravitates toward bold designers, sculptural tailoring, and gender-fluid styling that challenge traditional red-carpet norms. From major award shows to press tours and fashion weeks around the world, her style evolution tells a story of confidence, creativity, and cultural impact.

While speaking to Essence in 2020 about her style philosophy, Thompson said she believes there are “no rules in terms of dressing.”

She continued, “The seasons don’t dictate that you have to wear a coat. When I was growing up in high school, it was not uncommon for people to wear a pair of cutoff shorts and Ugg boots. Nothing made sense in relation to each other. If I can, I spend most of the year in New York because I love the way the seasons change. You get to really pull out a heavy coat and layer. I love that, particularly now that I’ve gotten more sensible about what I wear.”

For Tessa, “bold, fun, and interesting” are requirements when searching for clothing that lights up her wardrobe. She also loves working with young Black designers who are pushing boundaries in their field.

“We have so much fun together,” she gushed.

Here’s a look back at 10 of Tessa Thompson’s most unforgettable fashion moments over the years.

1. Futuristic Glam at the 2022 Venice Film Festival

In 2022, Tessa stunned on the Venice Film Festival red carpet in a dramatic Elie Saab haute couture gown that felt both timeless and sci-fi inspired. The ruby-red silk piece wrapped around her body like art, complete with a hood and sweeping train that shifted with every step, a bold choice that matched her fearless fashion persona. She paired the dramatic look with tights, pumps, a box clutch, and lipstick, styled courtesy of celebrity fashion architects Wayman and Micah.

3. Romantic Drama at the 2025 Critics’ Choice Black Cinema & Television Celebration

For the Critics’ Choice Association’s 8th annual celebration of Black cinema and television in December 2025, Tessa wore a Diotima Spring/Summer 2026 dress with rich textures and vibrant colors. The organic silhouette — a bubbling vermillion skirt and contrasting pink satin heels — echoed the evening’s passion and complemented her Actress Award for film honor.

4. Dominatrix-Inspired Chanel Gown At The 2019 Met Gala 

At the 2019 Met Gala, Tessa opted for a dramatic Chanel gown, showcasing sculptural tailoring in an avant-garde fetish gown. Speaking about the inspiration behind the look, Tessa’s longtime stylist Micah told Variety that the actress “really wanted to focus on female light as a vision of strength and a position of authority, whatever that looked like, however that could feel.” He added, “She’s grown up a strong woman her entire life; she’s been surrounded by strong, independent women. She wanted to play to that and have that, but still have fun with it.”

Tessa also commented on the look during an interview with The Hollywood Reporter, saying she felt like an “S&M doll” in the powerful outfit.

The actress wore minimal accessories, allowing the gown’s craftsmanship to shine. 

5. A Dreamy White statement gown at the 2014 Gotham Awards

Tessa Thompson delivered ethereal elegance at the 2014 Gotham Independent Film Awards in an Ashi Studio ensemble that felt straight out of a fashion fantasy. She wore a white cashmere gown adorned with delicate sequins and crystal embellishments, topped with a peach-toned, cropped overlay that cascaded into a dramatic, flowing train. Silver sequined pumps added a subtle shimmer that perfectly finished the look.

6. Atelier Versace Glamour at the 2020 Vanity Fair Oscar Party

For the 2020 Vanity Fair Oscar Party, Thompson embraced sleek, modern glamour in a one-shoulder mint green gown by Atelier Versace. The design featured striking black belt accents and a thigh-high slit, blending softness with edge. She styled the look with black gladiator sandals and a structured black box bag, giving the outfit a cool, contemporary finish.

7. Commanding Attention in Valentino at the 2018 Creed II Premiere

Tessa Thompson was impossible to miss at the European premiere of Creed II in 2018, arriving in a dramatic moss-green Valentino gown. The dress featured a high neckline, a dropped waist, and an expansive, voluminous skirt, creating a powerful silhouette. The rich color and architectural shape cemented the look as one of her most memorable red-carpet moments.

8. Black and White Ensemble during 2019 Paris Fashion Week

In 2019, during Paris Fashion Week, Tessa paired a black-and-white mini dress adorned with white bows with black trousers and tall kitten heels, balancing haute couture with downtown cool. The look felt both wearable and editorial. 

9. Zebra-Print Versace Suit at the 2019 Men In Black: International Premiere.

That same year, while on the press tour for Men in Black: International, she turned heads in a tailored Versace animal-print suit. The bold pattern and confident styling showed her flair for playful, unexpected tailoring. 

10. Valentino Rainbow Gown at the 2017 Emmys

Tessa made a memorable red-carpet impact in a vivid rainbow gown by Rosie Assoulin at the 2017 Emmys. Its pleated lurex and cutouts were an early signal that she would embrace fashion as a form of storytelling. 

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