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Will Smith’s Style Evolution, From the 1980s to Now

As we enjoy the success of "Bad Boys: Ride or Die," let’s look back at the style evolution of one of Hollywood's biggest stars

Despite Will Smith becoming a controversial figure because of the infamous Oscars slap, the “Bad Boys” star is still a beloved actor to Black folks. “Bad Boys: Ride or Die” is a summer hit and Smith is promoting the movie like the movie star he always has been.

With that in mind, let’s take a look back at his style evolution, from “Fresh Prince” to “Bad Boys.”

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1980s

Photo: Getty Images Al Pereira/Getty Images/Michael Ochs Archives

Prior to becoming a star on the big screen, Will Smith was a hip-hop star as a part of the duo DJ Jazzy Jeff & the Fresh Prince. As you can see, his style was much more flashy, befitting of a rap star trying to sell millions of records.

1980s

Photo: Getty Images Al Pereira/Getty Images/Michael Ochs Archives

One thing Will is always going to do is rep his city, so it’s no surprise he’s rocking a Philadelphia Sixers cap.

1980s

Photo: Getty Images Ron Galella, Ltd./Ron Galella Collection

Will could clean up, too. Just look at this dapper outfit from his appearance at the 1989 American Music Awards.

1980s

Photo: Getty Images MPIRock/MediaPunch

The Fresh Prince cleaned up nicely again here during his appearance at the 1989 VMA Awards.

1990s

Photo: Getty Images Chris Cuffaio/NBCU Photo Bank

When millennials think about Smith’s style, this may be the first image that comes to mind. Backward hat, colorful clothing, and Jordan 5s with no laces.

1990s

Photo: Getty Images Harry Langdon

It was the 90s. Baggy clothes and baggy suits were all the rage. The star opted to go for a more colorful suit to make this look pop.

S1990s

Photo: Getty Images Jim Smeal/Ron Galella Collection

Will could make anything look cool. He’s still fly despite looking like he’s about to go hiking.

1990s

Photo: Getty Images Bob Riha, Jr

Like the previous photo, if Will was going to show up in a baggy suit, it’s going to be flashy.

2000s

Photo: Getty Images Gregg DeGuire/WireImage

Although he was a family man at this point, he could still tap into his street style, as seen by this outfit above with his family on the red carpet.

2000s

Photo: Getty Images Giovanni Rufino/NBCU Photo Bank/NBCUniversal

Will Smith could always clean up with the best of them. He went for a nice, classic, clean-shaven look here with a timeless tuxedo.

2000s

Photo: Getty Images Elisabetta Villa

Burgundy suit jackets aren’t for everyone. But Smith seems to tie the look together with a Black turtleneck and purple scarf.

2000s

Photo: Getty Images Frazer Harrison

The late 2000s were an interesting time in fashion. It’s when celebrities start to mix streetwear with casual and formal wear. The above outfit is a perfect example of this, as Will is seen wearing Jordans with an otherwise casual look.

2010s

Photo: Getty Images BORIS HORVAT/AFP

In support of his son Jaden’s starring role in, “The Karate Kid,” Will Smith looked sharp in a striped shirt and black blazer at the Paris premiere of the 2010 film.

2010s

Photo: Getty Images Bennett Raglin/BET

Looking debonair in this 2015 photograph, Will Smith continued to rock those colorful suits, just like he did in the mid-1990s.

2010s

Photo: Getty Images Kevork Djansezian/NBCU Photo Bank/NBCUniversal

A classic tuxedo always gets the job done on the red carpet, but not man actors pull it off as good as Will.

2010s

Photo: Getty Images Eric Charbonneau/Getty Images for Twentieth Century Fox

Nearing the end of the 2010s, Will started to take more risks with his style. Just look at this fit with the loud trench coat and leather pants. It works.

2020s

Photo: Getty Images Emma McIntyre

At the beginning of the 2020s, Will Smith started to take even more chances with this style. Not only is this tailored suit unique for the star, but the choice he made with his facial hair is also different for Will.

2020s

Photo: Getty Images Alberto Rodriguez/Peacock/NBCU Photo Bank

This is a dapper fit Will effortlessly perfects with this burgundy turtleneck and burnt orange jacket. Can’t say he stands out as much as Jaden and Jada, though.

2020s

Photo: Getty Images Axelle/Bauer-Griffin/FilmMagic

This most recent outfit during the premiere of “Bad Boys: Ride or Die” may be the most daring look on this entire list. And of course, Will pulls it off well.

2020s

Photo: Getty Images Manny Hernandez

Will Smith embodied his “Bad Boys” character Mike Lowry in this fit and truly looks like a fresh officer running the streets of Miami

Straight From The Root

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