A quintessential Y2K icon, Anna Kournikova fused sporty essentials with low-rise denim for a classic (and frankly, flawless) zoo-day outing in 2002.

To look at this photo of Anna Kournikova visiting the Melbourne Zoo on January 18th, 2002, is to be instantly transported back in time. It’s a flawless time capsule of an era—a moment when casual-cool was defined by a certain brand of unapologetic, athletic glamour. Here she is, in the midst of her global superstardom, proving that her off-court style was as influential as her on-court game.

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A breezy, sun-drenched Lauren Donzis debuts the “La Dolce Vita” campaign for Rowena Knitwear—a collection that feels less like fashion and more like a whispered summer secret.

There’s a certain cinematic quality to Donzis’s latest collaboration with Rowena Knitwear, a quality that instantly transports you to a languid summer afternoon. The collection itself, titled “La Dolce Vita,” is an effortless blend of relaxed sophistication and playful ease. Donzis, with her quiet magnetism, becomes the perfect muse for this aesthetic, showcasing pieces that blur the line between comfortable loungewear and chic ready-to-wear.

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For a date night at Giorgio Baldi, Ashley Benson fused subtle dark romance with a sleek, rock-and-roll edge that feels perfectly L.A.

There’s a subtle art to date-night dressing in Los Angeles—a delicate balance between polished and effortlessly cool. Ashley Benson, stepping out with her husband Brandon Jack James, has seemingly mastered this dark alchemy. The look is all in the details, a masterclass in modern, understated glamour.

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Anna Kournikova’s Miami night-out look—red dress, leopard sandals, and a white tote—was peak 2007: sporty, sultry, and just a touch unpredictable.

There’s a particular kind of Miami glamour that doesn’t scream—it smirks. And on September 11th, 2007, Anna Kournikova embodied that mood with uncanny precision. The former tennis star stepped out in Miami Beach wearing a look that was equal parts laid-back and calculated, a masterclass in early-aughts casual chic.

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