Libby Chessler's Chic Evolution: From 90s Mean Girl to Style Icon

Jenna Leigh Green, widely recognized for her portrayal of Libby Chessler in the beloved 1990s sitcom Sabrina the Teenage Witch, recently captivated audiences with a remarkable public appearance. Attending 'The Age of Disclosure' premiere in November 2025, the 51-year-old actress presented a sophisticated and contemporary style, a striking departure from her high-school queen bee character.

Her ensemble featured an elegant taupe maxi dress paired with a structured white cropped blazer and sleek ankle boots, embodying a minimalist chic aesthetic. This transformation highlighted her evolution from the sharp-tongued antagonist of the 90s to a poised style icon. The event itself was a star-studded affair, drawing notable figures from across entertainment.

Beyond her memorable role as Libby, Green has forged a significant career in musical theatre, notably starring as Nessarose in 'Wicked' on both Broadway and in Los Angeles. Her extensive stage credits also include national tours and acclaimed productions, showcasing her vocal prowess and dramatic range. Green continues to engage in screen acting and performance art, maintaining a multifaceted career while privately supporting various arts and advocacy initiatives.