Jaden Smith's personal style has always been a talking point — along with his esoteric tweets and eyebrow-raising soundbites. However, looking back at the artist's fashion go-tos — wearing womenswear, crop-tops, bleached hair, and head-to-toe tie dye — Smith's drip has always been way ahead of the game.

More often than not, he looks to Louis Vuitton; the brand cast Smith in a groundbreaking campaign that saw him rocking skirts for the SS16 womenswear collection. In light of his new album, CTV3, we review some of his best style moments over the years.

Getty Images / Rindoff Petroff/Suu

Back in 2018, Smith rocked up to the LVMH Prize wearing a suitable Louis Vuitton drip, featuring a teal/black leather bomber jacket from the womenswear collection paired with tight-fitting motorcross-esque drainpipes, a brown/gold boot, a monogrammed side-bag, and bleach blonde hair.

Getty Images / Gregg DeGuire / Stringer

Back in 2019, all the style barometers pointed to relaxed tailoring being the next big wave. Sadly, the dreams of offices being repopulated with elegant suiting was exchanged for most of us sitting at home in sweats. Nevertheless, Smith's look here was right on track, as it nailed the perfect midpoint between smart and casual with playful cross-over detailing, zips, a pair of gold-soled LV Archlight sneakers, and bleached brows — a look that sadly never caught on with the masses.

Getty Images / Paul Archuleta / Stringer

This outfit arrived at the time of Smith's Neo Yokio era, wherein he voiced the main character for Ezra Koenig's anime series about a demon-slaying aristocrat living in an alternative timeline of New York City. The high lapels and subtle chest logo give the blazer a kind of school uniform vibe, complemented with black/white LV archlights on foot and a buzz of bubblegum pink hair.

Getty Images / Bertrand Rindoff Petroff

Handbags have developed from a strictly womenswear department item into an enormous market in the menswear realm. Brands such as Bottega, Fendi, and Louis Vuitton have leveled up their accessory game to accommodate a menswear sphere that begged for something a little more elegant than a sidebag to carry their stuff in. Here, Smith has tied up a cashmere wool blend double-monogram jacquard jacket with the Louis Vuitton Toupie handbag, notable for its UFO-like shape - a perfect match for Smith's frequent alien conspiracy chat.