Will Smith and Jada Pinkett Smith dared to look bold at the “Devil in a Blue Dress” premiere in 1995, the year they started dating.

Smith chose a suit with distinct jacket and gray stripes. Conversely, Pinkett Smith opted for a blue two-piece that included a tight skirt and a top that resembled a bra with strings that encircled her waist.

They were planning their looks for red carpet events by 1997. At the Soul Train Music Awards, they did just that.

That evening, Smith wore a cream-colored suit that went well with Pinkett Smith’s white halter dress.

At red carpet occasions, they would occasionally even wear the same color. Together, the duo wore lime green to the 69th Academy Awards.

Smith wore a conventional suit, but his colorful undershirt spoke otherwise. Pinkett Smith wore it with a metallic crop top and matching skirt that were encrusted with green glitter.

Even in 1998, when Pinkett Smith was expecting their son Jaden Smith, they kept up their identical fashion sense.

Together, they looked amazing at the Blockbuster Awards, sporting a lot of ’90s fashion elements.

Pinkett Smith donned a silver flowery duster over a strapless gown, while Smith wore a leather jacket and dress pants.

However, as evidenced by their 1999 Grammy Awards attendance, they continued to have their own sense of style.

On that particular night, Pinkett Smith wore a sleeveless yellow gown with a triangle cutout at the bodice and a thigh-high slit, while Smith wore leather pants and a shiny gray jacket.

She accessorized with black sandals featuring crossed straps and a matching headpiece.

However, the pair took sure to celebrate each other in various ways even when they didn’t dress alike, as seen in 2000.

Smith juxtaposed Pinkett Smith’s white and pink ensemble with a red leather jacket on one red carpet appearance.

However, as a tribute to her spouse, she had a lip-shaped tattoo on her shoulder that matched his garment and was adorned in red rhinestones. 

Here and there, they coopted historical red carpet ensembles, as seen at the 2022 Broadcast Film Critics Awards.

That evening, Smith dressed a white suit with a dark shirt and tie to match. Pinkett Smith also had a sophisticated appearance in a knee-length skirt and black halter dress with a plunging neckline.

In 2003, they began to display a more laid-back aspect to their relationship style.

At the “The Last Samurai” premiere that year, they both wore brown leather coats and pants on the red carpet.

When the couple arrived at Vanity Fair’s after-party in 2004 sporting opulent ensembles, their Oscars style began to take shape.