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“To inspire someone — to maybe give them some confidence to be fun and to explore and be powerful — there's nothing better in life for an artist.” Ahead, May, who also created the indelible costumes in iconic ‘90s movies — Romy and Michelle’s High School Reunion , Never Been Kissed , and The Wedding Singer — discusses what fashion job Cher would have in 2025, how to channel ‘90s style without looking like you’re wearing old clothes, and why Will Ferrell made her laugh during his Night at the Roxbury fittings

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