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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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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Never one to miss a moment for creative expression, Kelly Rowland fused vacation-ready staples—think wide-brim hats and bold prints—with her signature polished swagger, making the parking lot her personal runway.

The genius of Kelly Rowland’s style lies in her ability to elevate the everyday. What for most of us is a quick stop at Big 5 Sporting Goods followed by a treat for the kids becomes, in her hands, a bona fide street-style moment. There’s an unexpected brilliance to this look, an artful high-low mix that feels both effortless and entirely intentional.

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