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Celebrating 150 years since the inaugural Kentucky Derby in 1875, the event has evolved to place as much emphasis on spectacular outfits as it does on the actual racing

Chad Alexander and Georgia Benjamin brought out the Longines starting line-up

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Historical Roots: In Ancient Greece , women wore garments like the chiton and peplos , which were often draped over one shoulder, especially for more formal or ceremonial attire

Aaliyah Aaliyah mastered streetwear long before the term became a fashion phenomenon, as evidenced by her Tommy Hilfiger yellow tracksuit in 1997