From wiggle to A-line, mini to peasant, dresses are perhaps the most endlessly expressive item of women’s clothing. It’s perfectly okay to wear some dresses only once (wedding dresses fall into that exclusive category) while other dresses are intended to be workhorses (some women seem to live in their little black cocktail dresses). As for a good vintage dress, one with classic lines and timeless styling, it can be worn for years, even decades, after its alleged prime.

Let’s start with those workhorses, cocktail dresses. In order to be versatile, they must be able to be paired with almost anything, which is why black cocktail dresses are so popular. Coco Chanel recognized this back in the 1920s, as did Christian Dior when he successfully shook the fashion world by its collective lapels with the 1947 unveiling of his New Look.

Other designers to gain acclaim for their dresses include Hubert de Givenchy, who created a form-fitting dress for actress Audrey Hepburn’s Holly Golightly character in “Breakfast at Tiffany’s.” Oleg Cassini designed an ankle-length evening gown in pale silk jersey for First Lady Jacqueline Kennedy. And Gianni Versace put Elizabeth Hurley in a post-Punk dress featured a dangerously plunging sweetheart neckline and was held together by nothing but outsized safety pins.

Sometimes designers used dresses to make architectural or artistic statements. For example, in the 1950s, Dior answered his own opulent New Look with a collection of pared-down A-line dresses, whose silhouette resembled the letter A. These dresses were quickly embraced by scores of other designers, who saw them as the fashion equivalents of the clean lines found in Mid-century Modern architecture and design.

In the 1960s, Yves Saint Laurent proclaimed his fondness for the work of the great geometric abstractionist painter Piet Mondrian by grandly appropriating the artist’s work as bold super graphics on his straight-cut dresses. Embroidered African-inspired Saint Laurent garments followed, as did collections based on another of his passions, the Ballet Russes.

Saint Laurent’s work was often very colorful, but it was dull, dull, dull compared to the silk print dresses and tunics of Emilio Pucci, whose palette ranged from relatively understated combinations of purple, aqua, and white to trippy floral patterns of pink, green, yellow, and orange.

High-school girls in mid-20th-century America often got their first taste of the power of fashion while attending their senior prom. White cocktail or party dresses were widely e...

Just about every department store sold prom dresses; you could even pick one up at Sears. Some of the 1950s and ’60s labels that were best known for excelling at the form included Emma Domb, Christian Dior, Mainbocher, and Will Steinman.

Last but not least were sweater dresses, which could be worn with tights or perhaps Levi’s underneath. For some reason, wide horizontal stripes were deemed okay on these tight-fitting sweater dresses, probably because the women who could pull off this style were slim enough to negate their potential unflattering effects.

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