Hailey Bieber And Kylie Jenner Rock Heeled Flip-Flops With Baggy Jeans And Parachute Pants

  • By Rico
  • Sept. 30, 2025, 8:59 a.m.

Fashion Icons in Sync

Hailey Bieber and Kylie Jenner are not just beauty moguls but also style icons with a knack for setting trends. Recently, the duo was spotted in Beverly Hills, both sporting heeled flip-flops paired with relaxed baggy pants. It's clear these two friends are influencing each other's wardrobe choices, adding a fresh twist to their outfits.

On a sunny Friday, September 19, the pair indulged in some skincare pampering while turning heads with their coordinated looks. Both chose black pants for the outing, adding a touch of chic to their casual yet trendy ensembles. Their choice of footwear – the heeled flip-flop – has been a staple in their summer wardrobe, proving its versatility as the season changes.

Hailey's Laid-Back Look

Hailey Bieber stepped out in effortlessly cool baggy black wide-leg jeans adorned with studs, a simple white tee, and a sleek brown leather jacket. Her signature black sunglasses added a touch of mystery to the ensemble. Bieber's choice of Toteme's $560 Leather Heeled Flip-Flops is a testament to her love for this stylish yet comfortable footwear.

Kylie's Edgy Ensemble

Kylie Jenner, known for her bold style choices, opted for wet-look parachute pants paired with a cropped black T-shirt. She accessorized with a large black leather bag, perfectly complementing her heeled flip-flops. Jenner's footwear of choice includes Amina Muaddi's Juliette Patent Kitten Thong Sandals and Manolo Blahnik's Leather Paterno Sandals, priced at $800 and $775, respectively.

"Even as fall approaches, both women appear to refuse to part with their favored footwear," a fashion insider noted.

Accessorizing with Luxury

Kylie was seen earlier this summer with a vintage 2001 Gucci by Tom Ford Snakeskin Drawstring Tassel Shoulder Bag, a rare find that recently sold for $2,695. Meanwhile, Hailey's go-to accessory is Jil Sander's $3,350 Medium Goji Soft Handle Leather Bag, adding a touch of luxury to her ensemble.

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As the fall fashion season kicks off, Jenner and Bieber's affinity for wide-leg jeans and parachute pants is sure to inspire countless autumn looks. Their ability to blend comfort with high fashion is what continues to make them style leaders in the industry.

Rico
Author: Rico
Rico

Rico

Rico covers how celebs craft image—on carpets, in airports, and on Stories. He pairs look IDs and styling credits with the mini-narratives driving buzz: relationships, rebrands, and comeback arcs.