melissa Leo

Photo: Marc Royce

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Melissa Leo
53, Actress

The award-winning Leo (she won the best supporting actress Oscar in 2011 for her role as the tough-loving, chain-smoking mom in The Fighter and an Emmy in 2013 for her memorable guest appearance on Louie) played attorney Toni Bernette on HBO's Treme. She will next be seen in the film The Equalizer in September.

Go-to outfit: Though she describes her personal style as "boyish and raggedy," Leo says she's gotten a crash course in fashion by "going to events where I'm expected to be a movie star." Her take-away? "Simple is better. I love a pencil skirt, asymmetrical tops make me look crooked, and I'm very high waisted, so '40s- and '50s-style clothes fit me well."

Style crush: "Kate Winslet is a great hero of mine. She has such a gracious way of presenting herself. She's not a stick-thin woman, and anywhere she goes, she turns up looking like a lady."

Advice she'd give her younger self: "Aging is a blessing and should not be shunned. This is the great gift of getting a little older: knowing how to behave, what to wear, and when to wear it."

Vest, Alvin Valley. Skirt, Antonio Berardi. Earrings and cuff, Elizabeth and James. Shoes, Pierre Hardy.