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.

Scroll down for video

Is that a dress? Jaden Smith was seen wearing what appeared to be a LBD during an outing in Calabasas, California on Thursday

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.

Androgynous: The 16-year-old son of actors Will and Jada Pinkett Smith donned a long sleeve little black dress which he styled with a white crocheted sleeveless top

Jaden proved that he is expanding his wardrobe closet to include women's wear when he shared a photo of himself wearing yet another T-shirt dress.

'Went To TopShop To Buy Some Girl Clothes, I Mean "Clothes",' he captioned a mirror selfie on his Instagram account on Wednesday.

In the snap, Jaden is wearing a long sleeve striped dress over dark harem trousers at a gym surrounded by exercise machines and a track.

Went To TopShop To Buy Some Girl Clothes, I Mean "Clothes" A photo posted by Jaden Smith (@christiaingrey) on Apr 7, 2015 at 10:32am PDT

'That Moment When Your Wearing A Dress With No Pants And You Swerve Way To Hard,' he wrote on his Twitter account on Thursday.

While Jaden was showcasing his one of a kind street style, his young Hollywood friends are soaking up the desert sun for the Coachella Music Festival this upcoming weekend.

Close pals Hailey Baldwin and Justin Bieber shared swimsuit-clad photos of themselves with Jaden's rumoured girlfriend Kendall Jenner on their social media pages on Thursday.