In a sleek black dress and windswept hair, Anna Kournikova fused athletic poise with pop sensuality—like tennis royalty moonlighting as a Bond girl.

Before Instagram made every athlete a brand, Anna Kournikova was already rewriting the rules. In this 2002 editorial photoshoot—likely part of her official calendar campaign shot by Bill Ling in Acapulco, Mexico—Kournikova trades her tennis whites for a sleeveless black dress with a plunging neckline and side detailing that hints at eveningwear with a sporty twist.

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Christina Applegate’s Edgy ’90s Vibe in 1991 Photoshoot

Christina Applegate, in a striking 1991 photoshoot, embodies the quintessential edgy glamour of the early ’90s. The image captures her with a bold, teased blonde hairstyle, a hallmark of the era’s rock-and-roll-inspired fashion.

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In a plunging black gown and sleek choker, Jennifer Aniston gave Old Hollywood a minimalist twist—equal parts Morticia Addams and Studio 54 restraint.

March 26, 2000. Vanity Fair’s post-Oscar fête at Morton’s in Los Angeles. Jennifer Aniston arrives with Brad Pitt, but it’s her look—not the power couple status—that steals the frame.

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