Kylie Jenner Revisits Early Streetwear Era in Chanel High-Top Sneakers and a Teal “Life of Pablo” Tee

Just weeks after her split from Tyga, Kylie Jenner stepped out in Malibu proving—as she often did during her early style-formation years—that no personal drama could overshadow her evolving fashion instincts.

In May 2016, the then-18-year-old was photographed heading into Planet Blue for a little retail therapy, serving a laid-back yet luxe streetwear look that perfectly captured the mid-2010s blend of athleisure, graphic tees, and quiet-luxury accessories.

What makes this outing especially fun to revisit nearly a decade later is how clearly it illustrates Kylie’s emerging taste for high-fashion staples, particularly Chanel footwear. Her white Chanel high-top sneakers—part of the brand’s 14C collection—grounded the entire outfit, transforming a simple tee-and-shorts combo into something unmistakably designer.

Kylie Jenner keeps it casual in a teal “Life of Pablo” tee, denim cut-offs, and white Chanel high-top sneakers while shopping in Malibu on May 27, 2016 (Credit: WENN)

Even then, Kylie understood the power of a statement sneaker, and this moment reads today like an early preview of the sneaker-led “luxury casual” aesthetic she would later help popularize.

With her mix of vintage Chanel pieces and relaxed basics, Kylie showed how a great pair of shoes can elevate even the most effortless look—something that still defines her personal style years later.

Kylie Jenner’s Vintage Chanel Backpack Steals the Spotlight

The American reality television personality accessorized her casual ensemble — an oversized Life of Pablo T-shirt and denim shorts — with vintage Chanel pieces.

Kylie Jenner’s white vintage Chanel backpack

This is not the first time we’ve seen her carrying this vintage bag.

Kylie Jenner’s white vintage Chanel backpack featuring a drawstring closure with gold-tone hardware, a tonal designer logo detail, a rear zip pocket, and two leather shoulder straps

She posted a selfie showcasing the purse, a part of her enviable backpack collection, on Instagram a couple of months ago.

Kylie Jenner showing off her Chanel backpack with momager Kris Jenner on February 6, 2016 (Credit: Kylie Jenner’s Instagram)

The Blue Ferrari That Made Headlines

She also shared an Instagram photo wearing a ‘Life of Pablo’ t-shirt while posing next to the birthday gift from her former beau.

Kylie Jenner wears a “Life of Pablo” t-shirt to show off her blue Ferrari (Credit: Kylie Jenner’s Instagram)

The 18-year-old American reality television personality, socialite, and model posed in front of her $260,000 Ferrari — yes, the white one Tyga gifted her for her 18th birthday — that she recently had painted blue.

Kylie Jenner’s foundation contrasts with her pale skin as she admires her new blue Ferrari (Credit: WENN)

Casual Street Style: T-Shirt, Shorts, and Chanel Sneakers

Kylie was later seen shopping with friends at Planet Blue.

Kylie Jenner wears an oversized blue t-shirt and sneakers as she shops with friends in Malibu (Credit: WENN)

Makeup Mishap or Lighting Fluke?

For all the color-coordinating she did, Kylie seemed to miss the opportunity to match her makeup.

Kylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offs (Credit: WENN)

From some angles, her foundation appeared several shades darker than her neck — was it a makeup mishap or just unflattering lighting?

Kylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offs (Credit: WENN)

Ostentatious lifestyle and poor makeup blending aside, it was refreshing to see Kylie dressed in a regular t-shirt, denim shorts, and sneakers, like a typical teenager.

Kylie Jenner accessorizes with sunglasses and bracelets during a Malibu shopping trip (Credit: WENN)

Chanel Sneakers Take Center Stage

It was also lovely to see her just kickin’ it and having fun with her non-Hollywood friends.

Kylie Jenner wears Chanel sneakers with a casual shorts-and-tee look (Credit: WENN)

At the time, Kylie was just 18 years old—already a Lip Kit creator and rising fashion mogul.

Kylie Jenner’s feet in white Chanel zip-top sneakers (Credit: WENN)

Kylie Jenner felt blue in these retro-inspired Chanel zip high-top sneakers.

White Chanel Zip High-Top Sneakers

At first glance, the Kardashian-Jenner family and the house of Chanel might seem like cultural opposites—one thrives on reality TV and social media spectacle, the other on heritage, exclusivity, and refined taste.

Yet, despite their starkly different brand identities, both are undisputed powerhouses in shaping the fashion and pop culture landscape. And when these two forces collide, the results are always headline-worthy.

Revisit More Standout Chanel Fashion & Footwear Moments

Before we wrap, here are more Chanel-focused looks and Kylie-adjacent moments that highlight how the brand continues to shape celebrity fashion.