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“Clothes make the man,” said Mark Twain. “Naked people have little or no influence on society.” Women tend to take their fashions a bit more seriously: “While clothes may not make the woman,” said cosmetics entrepreneur Mary Kay Ashe, “they certainly have a strong effect on her self-confidence—which, I believe, does make the woman.”

Regardless of how you feel about the clothes you wear and the effect they may or may not h...

Fashions from the 1920s imbue one with a sense that is more carefree, thanks to the loose beaded tops and still-stylish cloche hats that characterized the Flapper era. Austerity ruled women’s fashions throughout the Great Depression and World War II, as the occasionally androgynous styles of the ’20s got downright masculine. After the war, Christian Dior focused on femininity by introducing his New Look, which swaddled women in miles of luxurious fabric.

Fashions from the 1950s translate especially well to the needs of women today. Those Chanel suits look every bit as smart as they did when the great Parisian designer updated her own creation in 1954. Vintage cashmere sweaters can be paired with everything from faded Levi’s off the rack to shiny Capri slacks. And period-perfect little black dresses with matching pumps will make you stand out at any cocktail party.

Sixties fashions are even more a part of our contemporary culture. You can go the short-skirt-and-tall-boots route, repurpose the brightly colored resort wear of Pucci, or slip into an Yves Saint Laurent tuxedo jacket, which can be worn as a suit or a separate for perhaps the ultimate in self-confident looks.

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