Rihanna, ever the trendsetter, fused cozy textures with luxe accessories—her fiery red hair and monogrammed Louis Vuitton backpack sealed the street-style moment.

There’s a kind of fashion fluency Rihanna possesses that makes even the most casual exit feel editorial. On September 29, 2010, as she stepped out of the Trump Soho Hotel in New York City, she delivered a look that was equal parts comfort and catwalk—a visual reminder that street style, when done right, can rival any red carpet.

Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 1 Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 2 Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 3 Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 4 Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 5 Rihanna Unveils Effortless Chic Leaving Trump Soho NYC – Sept 2010 - 6 Elyse Hofer Unveils Effortless Summer Chic for ZAFUL - 7

In the world of commercial modeling, every detail is intentional. And this image of Elyse Hofer is a lesson in summer clarity. The setting is a classic marina, the sunlight is perfect, and the swimwear—a simple yet effective two-piece bikini—is the hero.

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In a moment that fused ancient drapery with modern swagger, Rihanna debuted a beautifully pleated look (a true sartorial surprise) for a New York dinner.

Rihanna has always had a preternatural ability to pull from the archives of style—to find a thread of history and weave it into something so now, so completely her own. A prime example? This off-duty look from August 19, 2010, at a restaurant in New York City. It wasn’t a red carpet, but she transformed a simple dinner into a fashion moment of decadent, historical flair.

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