Men's

Jaden Smith's 10 Boldest Fashion Moments

To celebrate the talent's 24th birthday, here are some of Jaden Smith's most ambitious outfits. 

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Smith at the 2016 Met Gala.

As the child of legends Will Smith and Jada Pinkett-Smith, stepping out from under his parents' shadow wasn't easy, but Jaden Smith has made a name for himself in the fashion industry. His creative persona shines through as his keen eye for pattern mixing and penchant for ignoring gender norms make him a constant source of conversation on the red carpet and city streets alike.

The actor, musician, and activist has always favored bold looks, but his 2016 Vogue Korea photoshoot gained notoriety on Twitter when he donned a skirt and dress for the editorial. Now, gender-bending fashion has become a staple for Smith as he frequently rocks traditionally feminine pieces just as easily as a pair of jeans. His risk-taking has clearly paid off, as he now has a collection with New Balance and co-founded a fashion collective, Msftsrep along with his sister—and our July 2021 cover star—Willow, and Moises Arias and his brother, Mateo. As Smith celebrates his 24th birthday, look at some of his most boundary-pushing ensembles.

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Smith in a skirt suit from his fashion brand with sister Willow, Msftsrep.
This colorful jacket and sunglasses moment pops on the red carpet of the 2020 MTV VMAs.
At the 2018 Met Gala, Smith rocks the red carpet in this shearling Louis Vuitton coat, worn over white jeans and a Msfts tee.
Never one to shy away from making a statement, Smith shows up to the 2017 Met Gala carrying his locs.
Smith expertly layers a blazer over a cat-printed coat, mesh top, and skinny jeans at the 2016 MTV Video Music Awards.
For his 'Vogue' Korea editorial in 2016, Smith makes headlines by wearing traditionlly female elements: a black A-line skirt, blue nail polish, and a flower in his hair.
Even simpler outfits look intriguing on Smith—here, he wears Louis Vuitton at the brand's 2017 Cruise show.
No Coachella outfit is complete without a flower crown, and Smith doubles down with a coordinating floral-print tee.
Smith and his sister Willow both sport dresses in 2015 at the Olivier Rousteing & Beats event in LA.
A pro at mixing patterns, Smith wears this constrasting ensemble to the premiere of Justin Bieber's "Believe."
Unafraid to make a statment— Smith's distinguished street style features a bold, virant colored tie-dye pant and electric blue top.
An expert at an elevated denim look— Smith pairs these '90s-inspired baggy bottoms with a summertime floral sweater vest.
Simple yet sophisticated— Smith explores an elevated take on the classic black suit.

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