Jaden - who has been linked to both Kylie, 17, and Kendall Jenner, 19 - donned a long sleeve little black dress which he styled with a white crocheted sleeveless top.
Underneath his eclectic frock were dark colored cutoff jean shorts for a unique androgynous look.
The older sibling of Willow Smith accessorized his getup with cheetah print high socks, black and white Nike Flyknit sneakers and a black backpack over his shoulders.
He appeared to be in good spirits as he sported a beaming smile on his face.
Jaden Smith has always taken interesting fashion risks - what else do you call zebra-print harem pants and plaid print belts?
But the 16-year-old actor's new move is one of his most daring.
The son of actors Will and Jada Pinkett Smith wore what appeared to be a black woman's dress over a pair of distressed denim shorts during an outing in Calabasas, California on Thursday.
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