See All Of Jada Pinkett Smith's Boldest Looks

Jada Pinkett Smith is one of Hollywood's leading style icons because her style mantra is "try anything." While being in the public eye the last couple of decades, Pinkett Smith has tried on just about every aesthetic under the sun. One night she puts on something sinful by Versace, the next she dons a vintage 1950s Lanvin ballgown, and by the end of the week she is wearing a studded leather jacket with fur cuffs. Pinkett Smith is a style legend because she's open to new looks and aesthetics, and allows herself to experiment in her closet.

1. 1995 Premieres

In 1995, Jada Pinkett attended the Devil in a Blue Dress premiere with her then-boyfriend, Will Smith. She came appropriately dressed, literally wearing a blue dress! This was when the couple first began dating, so everyone was abuzz about their red carpet appearance. Which meant that Pinkett's dress hit a number of headlines the following day. She wore a two-piece knit dress, which consisted of a maxi skirt and a bra top that wrapped down her stomach. She also had a matching blue knit knapsack slung across her back.

2. 1997 Oscars

Pinkett Smith has never been one to follow the rules or to shy away from bold fashion choices. That's why she made such a statement when she arrived at the 1997 Oscars. While most starlets wore sweeping ball gowns and floor-length dresses, Pinkett Smith arrived in a slinky two-piece dress. The chain-mail Versace gown consisted of a crop top and a low-rise maxi skirt, which sported a gold chain above her hips.

3. 1997 MTV Video Music Awards

Pinkett Smith stole the show at the 1997 MTV Video Music Awards when she wore a bold and edgy outfit. Her look consisted of a corset with a bra peeking out from underneath, leopard print, a fur stole, and fishnet gloves. The outfit was so memorable that we're still talking about it decades later. She was 26 years old when this photo was taken, and she was best known for movies like The Nutty Professor and Set It Off. But that year, Jada would be in headlines for more things than just fashion. In 1997, she and Will Smith not only announced their engagement, but that they were also expecting their first child together.

4. 1998 Golden Globes

Pinkett Smith looked stunning at the 1998 Golden Globe Awards when she wore a bronze metallic dress that she paired with a crushed velvet stole. The dress was slinky and adorned with delicate bead work, creating an elegant and somewhat ethereal look.  That year, Pinkett Smith also stunned reporters on the red carpet when she introduced herself as "Jada Smith." . "I did it for Will," she said in the May 1998 issue of InStylemagazine. "It was my cute little introduction to our married life. He didn't know I was doing it. He didn't go to the awards, so he saw it on TV."

5. 1998 Grammy Awards

Pinkett Smith arrived at the 1998 Grammy Awards pregnant with her and Smith's oldest son, Jaden. The mom-to-be looked gorgeous in a sparkling gown which had sheer brown panels on the sides. That year, Will Smith won the award for Best Rap Solo Performance for "Men in Black," and Jada beamed from her seat as he went onstage to accept his award.

6. 1998 Blockbuster Awards

Pinkett Smith arrived at the Fourth Annual Blockbuster Awards in 1998 wearing a chic black dress over her pregnant belly. She spiced up the simple frock with a floor-length silver brocade coat and platinum blonde hair. That year, Pinkett Smith was up for the Favorite Supporting Actress - Horror award for her work in Scream 2. She lost to Sarah Michelle Gellar, who played in I Know What You Did Last Summer, but we're still buzzing about Pinkett Smith's red carpet look decades later.

7. 1999 Grammy Awards

Pinkett Smith decided to go with something slinky for the 1999 Grammy Awards, and donned a gold cutout dress designed by Eduardo Lucero. The daring dress had an asymmetric neckline and was accented with cutouts at the waist and a long slit at the skirt. She paired the look with a matching head wrap and chic, tiny sunglasses. 

8. 2001 Premieres

In 2001, Pinkett Smith arrived at the Kingdom Come premiere wearing an all-beige outfit that was the epitome of the early 2000s. The look consisted of a beige leather jacket and beige culotte pants that floated just above the ankles. She brought the look together with an extra large, boxy purse. Then to give the look some spice, she accessorized the outfit with a chunky choker necklace and blue tinted sunglasses. It was the perfect post-Y2K outfit.

9. 2001 Burberry Store Opening

In 2001, Pinkett Smith arrived at the Burberry Beverly Hills store opening and benefit party wearing an edgy Burberry look. She wore head to toe leather, donning a leather jacket and boot cut leather pants. She paired the jacket with a crisp white shirt, which had Burberry's trademark plaid on its oversize cuffs. It was the first store in Beverley Hills for the British clothier, and Hollywood stars came in droves to support it. Pinkett Smith's outfit proved that the traditional brand was having something of a comeback.

10. 2002 Oscars

The 2002, Oscars night was an important evening for the Smiths. Will was nominated for an Oscar for his role in Ali, a movie in which Jada also starred in. Her publicist, Karynne Tencer, searched the internet for a memorable and unique dress, and found this vintage Lanvin yellow gown for sale. It was a 1950s Antonio Canovas del Castillo for Lanvin creation, but Jada had some reservations. 

11. 2003 'The Matrix Reloaded' Premiere

Pinkett Smith joined the legendary Matrix cast during its second edition, and she showed up to the premiere wearing an outfit worthy of the movie. Pinkett Smith donned a black cocktail dress, which she accented with a leather and fur coat. The memorable leather jacket was decorated with studded patterns and prints.

12. 2003 'The Matrix Revolutions' Premiere

In 2003, Pinkett Smith walked the red carpet at The Matrix Revolutions premiere in Los Angeles. She changed up her look from the other premiere, leaving the leather jacket at home and opting for a simple evening gown.

13. 2004 'Collateral' Premiere

Pinkett Smith was on a gold kick in 2004, which was proven with this Collateral premiere gown she wore in Berlin. She dazzled in a sequined midi gown that had embellished tassels dancing down its front. She matched the sleeveless dress with gold strappy heels, along with gold chandelier earrings. 

14. 2004 Oscars

Pinkett Smith looked like a dream at the 2004 Oscars, donning a "super feminine" Valentino dress. (Her words.) The actor told Varietythat in the past she and her husband liked to coordinate their outfits, but now they do their own thing. “And by golly, most of the time it ends up looking like we actually coordinated!” she said.

15. 2004 Hollywood Awards Gala

The best thing about Pinkett Smith is that she doesn't subscribe to a certain style. She wears everything from princess ballgowns to leather jackets to revealing slips. While she donned a romantic Valentino dress at the Oscars, Pinkett Smith switched gears at the Hollywood Awards and wore a revealing evening gown that had a leg slit that went all the way up to her rib cage. While some thought the dress was risque, the actor pulled it off flawlessly.

16. 2005 'Hitch' Premiere

Everyone loved Will Smith's 2005 rom-com Hitch, in which he starred alongside Eva Mendes. But while the funny one-liners were memorable, so was Pinkett Smith's premiere dress. She wore an orange silk gown with glittering embroidery across the top. But you didn't see that detail straight away, since she also wore a fabulous fur and leather jacket, which had statement fur cuffs.

17. 2005 BET Awards

In 2005, Pinkett Smith arrived at the BET Awards wearing a stunning chain link dress. Both she and Will Smith were hosts that night, so all eyes were on what Pinkett Smith was wearing.

18. 2006 Redbook's Strength & Spirit Awards

Pinkett Smith went dressed demure and ladylike to the 2006 Redbook's Strength & Spirit Awards. She was one of the honorees, and wore a white frilly mini dress and a black trench coat. She looked very Parisian in her feminine ensemble.

19. 2007 Oscars

Pinkett Smith channeled the Oscars statue at the 2007 Academy Awards. She wore a stunning Carolina Herrera dress, but it was a stressful night for the actor. That year the ceremony was a family affair, since Will Smith received a nomination for The Pursuit of Happyness, which also starred Jaden.

20. 2009 Vanity Fair Oscar Party

Pinkett Smith looked like a goddess at the 2009 Vanity Fair Oscar Party, where she wore a one-shouldered gown with a long, sweeping sleeve that mimicked her elegant train. It was a Roberto Cavalli Resort gown with crystal detailing on the waist.

21. 2010 American Music Awards

Pinkett Smith wore a custom-made Emilio Pucci gown to the 2010 American Music Awards. She is a devoted fan of the label, and constantly wears the designer's creations to red carpets and major events. This particular Pucci dress was sent down the runway in all black, but was recreated into a bronze and orange version for the music awards.

22. 2014 Oscars

Pinkett Smith worked with Versace to create her custom-made gown for the 2014 Oscars. “I really wanted to do pink, and I wanted to do something that was Old Hollywood glamour,” she told Variety. She chose this particular dress from a selection of sketches. “I just love Versace — they’re my favorite in regards to awards season because they just never fail me, ever.”

23. 2015 'Concussion' Screening

Pinkett Smith pulled out all of the stops for the 2015 screening of Concussion, wearing a "naked dress." The silver see-through dress was created by Zuhair Murad, and featured star burst embroidery and a tinsel skirt. 

24. 2016 Global Citizen Festival

Pinkett Smith attended the 2016 Global Citizen Festival in Central Park, which raised money to end extreme poverty by 2030. For the event, the actor donned a playful mini dress that had a variety of busy patterns.

25. 2017 Essence Festival

Pinkett Smith dressed like the style icon she is at the 2017 Essence Festival. She wore a striking see-through shirt with fan embroidery, along with a knee-trailing bow belt.

26. 2017 BET Awards

Pinkett Smith shut down the 2017 BET Awards in her metallic gown by Alexandre Vauthier. The slinky number featured a low-cut neckline and a high slit — and the sassy gold scarf around her neck took the siren look to another level.

27. 2017 NBA Awards

Pinkett Smith has a fun sense of style, as this evening dress proved. She donned a feather and sheer gown to the 2017 NBA Awards. The dress was made by Sophie Theallet, and it consisted of a mini with a metallic lace maxi overlay. As always, Pinkett Smith looked sexy, bold, and playful all at once, and left a memorable impression on the red carpet.

28. 2019 'Jimmy Kimmel Live' Appearance

Pinkett Smith arrived at the Jimmy Kimmel Live show in 2019 wearing a stunning pant ensemble. She wore satin green pants and a matching satin bandeau top, with a chain-link mesh tank on top.

29. 2019 Grammy Awards

Pinkett Smith raced to the top of every best dressed list at the 2019 Grammy Awards when she showed up wearing a bodysuit-turned-feather-gown. The pink dress was a perfect mixture of couture, flapper style, and "Vegas show girl," and was created by Roberto Cavalli Couture.