The cocktail dress is one of these rare articles of clothing that must be special enough to make an impression at a variety of events, yet versatile enough to be worn time and time again. It’s no small feat, which is why the most famous and popular form of cocktail dress is a true classic—the little black dress.

Coco Chanel was not the first designer to put her clients in a black dress, but she was the first to finally wrench black from its associations with mourning and reinvent it as the preferred color for festive, carefree occasions. In the mid-1920s, her simple, straight, one-piece calf-length dresses received almost universal acclaim, becoming the uniform of sophisticated swells throughout the decade and into the Great Depression, when it was admired as much for its economy as its style.

After World II, Christian Dior did not neglect the cocktail dress when he unveiled his New Look, although his creations used miles more fabric than Chanel ever would have contemplated. By the 1950s, though, the black cocktail dress seemed almost risqué, a crass instrument of seduction when compared to the innocent circle skirts of teenage girls, to say nothing of the frumpy house dresses worn by their stay-at-home-moms...

Even so, sleeveless cocktail dresses from the 1950s ranged from those basic black numbers favored by film sirens and vixens to only slightly less modest wiggle dresses in metallic brocade. Cotton prints with arms that stopped above the elbow, with peekaboo details around the waist, were also common. At some parties, purple lace dresses (tight at the waist, flared at the hem, and accessorized by multiple strings of pearls) would frequently square off against strapless numbers in baby blue chiffon.

For 1950s girls attending the high-school proms, white cocktail or party dresses were widely embraced, but so were dresses in soft pastels. Although it was probably not self-evident at the time, these muted tones paved the way for the bold reds and blues that would become prom favorites in the 1980s and ’90s.

In the 1960s, though, the little black dress came roaring back thanks to a dress Hubert de Givenchy created for actress Audrey Hepburn, who played Holly Golightly in “Breakfast at Tiffany’s.” The form-fitting dress she wore for that film, with its thin straps over bare shoulders and a vent at the hem that exposed Hepburn’s leg to the knee, was so legendary that it sold at auction almost half a century later for just under a million bucks.

Givenchy’s cocktail dress for Hepburn is only one example of a prominent designer’s little black dress kick-starting a young actress’s career. For example, Elizabeth Hurley achieved almost equal notoriety in 1994 when she wore a Gianni Versace variation of the little black dress to a film premiere. That post-Punk creation featured a dangerously plunging sweetheart neckline and was held together by nothing but outsized safety pins.

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