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If the dress is simple, subtle texture on the tights works beautifully

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WEAR: Longline Wool Coat + Clutch Bag + Maxi Sweaterdress + Ballet Flats The secret to pulling off dresses in the winter comes down to having one staple on hand: a sweaterdress

Natasha Richardson The actress played one of the most stylish moms on TV in The Parent Trap and her fashion sense IRL was equally as good, as this blazer skirt (dress?) set proves

HOW TO STYLE: A classic LBD, perfect for any occasion

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 Michelles 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 youre wearing old clothes, and why Will Ferrell made her laugh during his Night at the Roxbury fittings