Sometimes, the most intriguing street style moments aren’t on a runway—they’re in the most unexpected places. For Kendall Jenner and Hailey Bieber, that place was a back-to-school shopping spree at Brandy Melville in Brentwood, California, on August 20, 2025.
Is it a high-low dressing masterclass? Or a subtle wink at the art of wardrobe contradiction? Darlings, it is both, and it is glorious.
For their shopping date, the two fashion titans, who have collectively helped define a generation’s aesthetic, presented a study in effortless, understated elegance. This wasn’t a case of flaunting logos; it was an exercise in the most refined form of celebrity fashion—the kind that only true insiders understand.
Kendall’s look was a masterclass in clean lines. She wore a charcoal gray midi dress that hugged her silhouette, a piece that felt at once simple and impossibly chic. She paired it with black criss-crossing toe loop sandals and, in her hand, the star accessory: a buttery brown leather tote, The Row’s Terrasse Bag. A touch of “noughties” nostalgia was added with rectangular sunnies. It’s a look that whispers of a sophisticated, almost European sensibility—pared-down, yes, but every element is intentional, considered.
Hailey, meanwhile, debuted her own version of elevated simplicity. Her look was built on wardrobe blocks we all know: an elevated strappy white tank top from Suzie Kondi and a pair of indigo low-slung jeans. But it was her accessories that told the real story. She wore Toteme’s Leather Heeled Flip Flops—a quiet luxury staple if ever there was one. Slung over her shoulder, a woven black leather bag, identified as The Row Small Woven N/S Tote Bag. And, of course, the ever-present Solow & Co. Oval Diamond Engagement Ring on her finger. This isn’t just an outfit; it’s a modern uniform for the discerning woman who values craftsmanship and quality over fleeting trends.
The irony of two of the world’s most popular celebrities stocking up on basics at a teen-focused brand is not lost on me. But this is the genius of their style—it’s relatable and aspirational at the same time. The essence of their style, and the secret to its success, lies in the perfect marriage of simple, accessible pieces with investment-worthy accessories. For more on the style moments that define a trend, explore our extensive celebrity street style archives.
A Guide to Acing the High-Low Look
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Invest in a Foundation: Build your wardrobe on high-quality, foundational pieces. A great-fitting midi dress or a perfectly-cut pair of jeans will anchor any look, giving it a polished feel.
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The Power of the Accessory: This is where the magic happens. A designer bag, a classic pair of shoes, or a unique pair of sunglasses can instantly elevate a simple look into something iconic.
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Embrace Textural Contrast: The outfits combine a mix of textures—smooth leather, woven leather, denim, and a soft knit dress. This adds depth and visual interest without needing loud colors or prints.
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Simplicity is Sophistication: Remember, true style is about nuance, not noise. By sticking to a simple color palette and minimalist design, the attention is drawn to the quality of the pieces and the confidence of the wearer.
