Just weeks after her split from Tyga, Kylie Jenner proved she was moving on in style. In May 2016, the then-18-year-old reality star stepped out for some retail therapy at Planet Blue in Malibu, turning heads with her laid-back, luxe streetwear look.
With her signature blend of high-end accessories and casual pieces, Kylie made it clear she wasn’t letting a breakup dull her shine.
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)
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 some vintage pieces from Chanel.
Kylie Jenner’s white vintage Chanel backpack (Credit: WENN)
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 (Credit: WENN)
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
You can achieve a similar look for just $69.95 with Steve Madden’s “Decaf” sneakers, available for order at Zappos.
White Steve Madden “Decaf” Sneakers, $69.95
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.
Chanel Moments: Kardashian-Jenner Style Icons in the Iconic Brand
The Kardashian-Jenner clan has long been associated with high fashion, and Chanel remains a staple in their wardrobes. Here are some standout moments where they showcased their love for the iconic brand:
Kendall Jenner’s Chanel Runway Appearance
- Event: Chanel Fall/Winter 2017/2018 Fashion Show
- Outfit: Kendall walked the runway in a chic ensemble featuring Chanel’s signature style elements.
- Footwear: She donned beige-and-black Chanel kitten-heel cap-toe mules.
- See more: Inside Chanel’s Runway: Gigi, Bella & Kendall’s Show-Stopping Looks
Kim Kardashian’s Barbie-Inspired Pink Chanel Cardigan
- Event: Outing in New York City
- Outfit: Kim channeled Barbie vibes in a pale pink Chanel cardigan paired with matching attire.
- Details: The look was complemented by rosy makeup and a baby-pink manicure.
- Discover more: Kim Kardashian Channels Inner Barbie in Pink Chanel Cardigan
Kourtney Kardashian’s Chic Chanel Waist Bag
- Event: Date with Younes Bendjima
- Outfit: Kourtney wore a white bralette and pants ensemble.
- Accessory: She carried a white Chanel waist bag, adding a touch of luxury to her look.
- Explore her style: Kourtney Kardashian Carries Chanel Waist Bag on Date with Younes Bendjima
Kris Jenner’s Chanel Perfume Bottle Bag
- Event: Fashion Week Appearance
- Outfit: Kris donned a stylish ensemble complemented by nude fishnet tights.
- Accessory: She carried a unique Chanel perfume bottle bag from the brand’s Cruise 2014 Collection.
- See her look: Kris Jenner Totes Chanel Perfume Bottle Bag in Nude Fishnet Tights
These moments highlight the family’s enduring relationship with Chanel, showcasing how each member incorporates the brand’s timeless pieces into their unique styles.