Jaden and Willow Smith’s Iconic Style Moments

When it comes to fashion icons, the competition in Hollywood is strong, but two stars who easily make the list are Jaden Smith and Willow Smith. The Smith siblings have become Gen Z tastemakers for their unapologetic aesthetic and for always pushing boundaries every time they step onto a red carpet. Their fearless experimentation spans everything from gender-fluid suiting to experimental makeup, and they’ve managed to turn every appearance into a cultural moment worth discussing.

Jaden Smith and Willow Smith have built their reputations on refusing to play it safe. Jaden recently stepped into his role as men’s creative director at Christian Louboutin, launching a fashion-forward footwear collection that reflects his innovative approach to design. Meanwhile, Willow continues to redefine what it means to be a cultural force, constantly inspiring new trends through her bold beauty choices and fearless silhouettes. Let’s take a look back at some of their most memorable red carpet moments.

Leather For Paris Fashion Week

At Paris Fashion Week, Jaden demonstrated why Christian Louboutin entrusted him with the label’s menswear direction. This worn-leather jacket paired with baggy cargo trousers and pointed shoes shows his ability to balance texture and silhouette. It’s the kind of outfit that looks effortless but is clearly the result of thoughtful styling choices.

Tailored Style

For the Vivienne Westwood show, Jaden arrived in an elegant pinstriped suit with pointed-toe shoes completing the look. If there’s one thing Jaden has mastered, it’s the art of a sophisticated, sharp suit that feels both classic and contemporary.

Willow’s Shirt and Tie

Willow’s approach to tailoring always includes a creative twist. At the Christian Dior show, she wore a crisp button-down with a tie wrapped around her waist as a cinching belt. It’s the kind of styling detail that transforms a basic silhouette into something entirely her own.

Cargo and Crop at Paris Fashion Week

Willow’s cropped shirt paired with a billowing cargo skirt stands out for its balance of proportion. What really elevates the fit is her makeup: a gold lip, smoky eyes, and razor-sharp winged eyeliner that adds drama without overwhelming the outfit.

Futuristic Makeup

When it comes to beauty, Willow’s approach centers on bold experimentation and color play. For a July appearance on “Jimmy Kimmel Live,” she wore shimmering blue shadow with pink and purple blush, creating a coordinated palette that feels futuristic without losing its accessibility.

Jaden’s Equally Bold Looks

Jaden also knows how to play with color and texture. During Paris Fashion Week, he attended the Christian Louboutin presentation wearing red from head to toe, with dark shades and silver jewelry providing sharp contrast. The monochromatic approach felt confident and deliberate rather than accidental.

Slaying Together at the Grammy Awards

For the 2025 Grammys, the siblings hit the red carpet with their individual style fully intact. Jaden wore a sleek black suit topped with a whimsical house sculpture, while Willow opted for a trench coat with black-and-silver lingerie visible underneath and a gorgeous, boxy afro. Together, they represented a new generation of artists willing to blur the lines between fashion and art.

Jaden’s Creative Vision in Footwear

Jaden recently launched a footwear collection with Louboutin, and his Plato Dots loafers demonstrate that his design sensibility extends far beyond red carpet appearances. In an interview with Hypebeast, he explained the concept behind the customizable polka-dot shoes.

“You want the shoe to be able to change and evolve, and you don’t want to have to keep on buying new shoes,” he said. “So, it’s like you just have white socks on; as soon as you put the shoe on, it kind of brings it new life.”

The philosophy behind the design reveals how Jaden thinks about fashion as functional art, not just aesthetic display.

Willow’s Gorgeous Afro

Willow consistently nails both fashion and hair moments simultaneously. Her stunning afro at Jordyn Woods’ wedding continues to dominate social media timelines. It’s natural, voluminous, and unapologetically beautiful—a far cry from the heavily styled looks that used to dominate celebrity culture.

Cornrow Queen

Her cornrows paired with curved black shades, a fur coat, and glittering eyeshadow created a look that felt ready for a stylish female “Men in Black” reboot. The accessories and hair work together to create a cohesive aesthetic rather than competing for attention.

Jaden Smith’s Checkered Skirt

Jaden has never subscribed to rigid gender norms in fashion. In 2022, he rocked a checkered skirt over gray trousers for a formal occasion, following in the footsteps of pioneers like Prince, Grace Jones, and Sylvester. He wore it like it was the most natural thing in the world, which perhaps is the point.

A Simple and Elegant Fit

For an event at the Grammy Museum in 2024, Willow dialed back the drama in favor of ease. A cozy turtleneck, a plain brown leather belt, and her natural afro created a look that felt grounded. Bright jewelry added just enough personality without overshadowing the overall simplicity.

Blazers and Baggy Jeans

Jaden proved that understated styling can be just as impactful as his bolder looks. A simple blazer, baggy jeans, and neatly braided locs created an outfit that felt effortlessly cool and perfectly tailored despite its casual appearance.

Willow’s Current Style

For the Spotify Best New Artist event, Willow stepped out in a sleek black wrap dress with one bare arm, paired with maroon heeled boots. Her dreadlocks tied into a high bun and minimal makeup let the silhouette speak for itself. Whether she’s experimenting with avant-garde high fashion or keeping things minimalist, Willow consistently delivers.