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Will Smith's 50 Most Stylish Fashion Flashbacks

50 photos
Aug 21, 2018 7:42 PM
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Will Smith
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Spread Pictures / BACKGRID

Grinning in Grey

The Men in Black actor flashed a peace sign at the camera as he stepped outside in a white cap and a grey jacket.


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Splash News

Sunshine Smile

Will was a ray of sunshine in his yellow tee as he flashed a bright smile to the crowd.


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Jackson Lee/ Splash News

Windbreaker Win

Sporting a grey outfit and blue jeans, the father-of-three headed out with his stylish wife.


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Pierre Suu/GC Images

Black Suit Stud

Wearing a black ensemble, the happy dad posed with his smiley daughter, Willow Smith.


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Theo Wargo/Getty Images

Plaid Icon

On May 23, 2012, the iconic duo attended the Men in Black 3 premiere at Zigfield Theatre in New York.


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Andreas Rentz/Getty Images

Golden God

Donning golden accessories, the movie star arrived at the Men in Black 3 in Berlin for the Germany premiere at O2 World on May 14, 2012.


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Chung Sung-Jun/Getty Images

Matching Pair

In Seoul, South Korea, the longtime lovebirds attended the South Korean premiere of Men in Black 3 on May 7, 2012.


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Michael Buckner/WireImage

JB Style

Wearing a gold metallic jacket and a bright orange shirt, the "Gettin' Jiggy Wit It" singer put his arm around a young Justin Bieber at the 25th Annual Kids' Choice Awards on March 31, 2012.


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Partners in Crime

The actor and Jay-Z attended the Gucci and RocNation Pre-GRAMMY brunch held at Soho House on February 12, 2011 in West Hollywood.


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Gareth Cattermole/Getty Images

Suited Up

The young family smiled on the red carpet as they wowed in bold outfits.


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Kevin Mazur/WireImage.com

Power Couples

Smiling next to his wife, Jay-Z and Beyonce, the Focus actor looked dapper in a tux at the 64th Annual Tony Awards at Radio City Music Hall on June 13, 2010 in New York City.


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Mark Von Holden/Getty Images

Sweater Weather

At the TEN Upfront presentation at Hammerstein Ballroom on May 19, 2010 in New York City, Will cuddled up next to his petite love for photos.


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Gregg DeGuire/WireImage

Metallic Mood

The actor was part of the star-studded crowd at the Beckham Welcome to LA Party at the Museum of Contemporary Art on July 22, 2007 in Los Angeles. Wearing a metallic suit and shades, the actor enjoyed the company of his wife, Tom Cruise, Katy Holmes, Victoria Beckham and David Beckham.


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Salvatore Laporta/Getty Images

Classy Duo

The Hitch actor and his sweetheart attended Tom Cruise and Katie Holmes' wedding on November 18, 2006.


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Lester Cohen/WireImage

Fedora Feel

Wearing a fedora and a white plaid suit, Will and his leading lady attended the 2005 BET Awards on June 28 at the Kodak Theatre in Hollywood.


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AP Photo/Kevork Djansezian

Beanie Baby

Wearing a comfy beanie, the two-time Academy Award-nominee kissed his wife at the premiere of Bad Boys II in Los Angeles on July 9, 2003.


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David Corio/Redferns

Classy & Cool

Will looked ready to drop a new beat with DJ Jazzy Jeff as the pair posed in slick leather outfits.


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SGranitz/WireImage

Velvet Hugs

Will wrapped his wife in a warm hug during a fun night out.


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Frank Micelotta/Getty Images

Pastel Accents

Will looked stylish in a yellow and blue-accented jacket, as he posed with his wife and Chris Rock.


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Jeff Kravitz/FilmMagic, Inc

Slime God

The Miami singer was all smiles after he got slimed at the 2000 Kids' Choice Awards.


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Paul Drinkwater/NBCU Photo Bank

Red All Over

Back during his days on The Fresh Prince of Bel-Air, the TV star was known for his legendary bright clothes, including this classic red outfit.


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Ron Galella, Ltd./WireImage

Leather Lovers

The newlyweds made their red carpet debut on March 10, 1998 at the Blockbuster Entertainment Awards in stylish leather looks.


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Kevin Mazur/WireImage.com

Kings of Philly

The hip-hop duo sported Phillies jerseys at the 40th Annual Grammy Awards in New York City on February 25, 1998.


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Ron Galella, Ltd./WireImage

Oversized Chic

The talented pair attended the Devil in a Blue Dress premiere on September 22, 1995 at the Academy Theatre in Beverley Hills.


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