1. Holly Golightly: In Truman Capote's novella Breakfast at Tiffany's, his heroine Holly Golightly is actually a high-class call girl. But Audrey Hepburn's cheekier, sleeker interpretation of Miss Golightly is what won over American filmgoers when it was released in 1961. Draped in enviable Givenchy gowns, diamonds and cocktail dresses, Hepburn also channeled a more relaxed 60s vibe during her "Moon River" scene, wearing a simple gray sweatshirt with her hair tied in a makeshift turban. The famous black Givenchy dress worn when Holly Golightly stops in front of Tiffany's was recently sold for 467,000£ at a London auction in December 2006.
2. Carrie Bradshaw: Candace Bushnell's vibrant characters in her based-on-the-column book Sex and the City became so popular that they were rewarded with their own TV show and two feature films. The series narrator is sex columnist Carrie Bradshaw, a feisty fashionista with a weakness for models, Fashion Week, shoes and designer clothing. Carrie's also known as a good vintage shopper, but her preference for Manolo Blahniks made the shoe designer a household name, and resulted in higher prices for his designs in the real world. Stylist Patricia Field is credited with developing fashion as its own strong character in the TV series, inspiring women to consider getting dressed as a true form of self-expression and evade head-to-toe looks.
3. Miranda Priestly: The title character in Lauren Weisberger's The Devil Wears Prada is said to be loosely based on the real-life magazine editor Anna Wintour, the so-called ice queen or editrix of American Vogue. Known for being an egomaniac with a faultless aesthetic, Priestly runs the fictional magazine Runway and makes her personal assistants' lives miserable. In the film version, audiences got to see Priestly's — played by Meryl Streep — fabulous wardrobe and even a glimpse into the famed Runway fashion closet. The film was also styled by Patricia Field.
4. Lady Brett Ashley: One of Hemingway's most complex female characters is the troubled but independent Lady Brett Ashley, an expat who lives in Paris and teases The Sun Also Rises' Jake Barnes even as she takes up with other men, including a young bull fighter in Spain. As Lady Brett Ashley miserably searches for conventional love and romance after WWI, she is still seen as a fashionable member of the upper class and is highly desirable to men; Hemingway writes that she is "damned good looking." Ashley isn't just on the cutting edge of fashion: she's a few steps ahead of the flappers of her day, choosing to wear tighter fitting clothes along with her hats and short haircut, emphasizing her masculine-like independence.
5. Scarlett O'Hara: Scarlett O'Hara is one of the most infuriating and endearing characters in American literature and film. Maragaret Mitchell created Scarlett, the strong-willed, spoiled Southern belle whose lifestyle is uprooted during the Civil War but who never compromises her flamboyant taste. Vivien Leigh played Scarlett in the 1939 film version of Gone With the Wind, just three years after it was published. From the white, puff-sleeved ball gown she wears at Tara to the green dress she has made from curtains, Scarlett's outfits are considered some of the most iconic in Hollywood filmmaking and American literature.
6. Gloria Gilbert: Writer F. Scott Fitzgerald and his wife Zelda were known as America's most fashionable couple during the 1920s, and their bizarre antics inspired a generation to live in the moment. Fitzgerald's most autobiographical work was the novel The Beautiful and Damned, in which he chronicles the highs and lows of the turbulent and exhausting relationship of the Gilberts. Gloria is young and impossibly fashionable, always dressing in furs and the latest fashions in New York. While the characters are ultimately doomed, their glamorous, opulent lifestyle gives the perfect picture of the frenzy of the Jazz Age.
7. Allie Hamilton: Nicholas Sparks' novel-turned film The Notebook isn't nearly old enough to be considered a classic, but its immediately intense popularity has made it an inspirational force in pop culture and fashion. The story centers around the lifelong love story of Allie Hamilton and Noah Calhoun, who first meet during the summer of 1940. Although the story is told through switches to the past and back to the present, the flashbacks in the film offer the best look at the feminine but progressive Allie, played by Rachel McAdams. Always dressed in silk sundresses, hats or hair accessories and pumps, Allie always takes care of her entire appearance, from her red nail polish to her bouncy curls. The film also inspired women around the country to experiment with easy retro looks during the mid-2000s.
8. Daisy Buchanan: Another tragic but still influential character from the 1920s is Daisy Buchanan, from Fitzgerald's The Great Gatsby. The delicate Daisy is trapped in an adulterous, sometimes abusive marriage even though she has a romantic past with her next door neighbor, Gatsby. Mia Farrow played Daisy in the 1974 film version, which is generally considered the best film adaptation of the novel. Farrow is dressed in ethereal cream and white silk and linen, usually with a broad-brimmed hat and wrapped in scarves.
9. Annie Hall: Diane Keaton's portrayal of the lively Annie in one of Woody Allen's most iconic films, Annie Hall, is still referenced and celebrated today. Annie's masculine costumes are constantly reinterpreted by actresses, models and designers who still love her slouchy khaki pants, vests, neckties, hats and blazers, and that have translated well for those who would rather eschew traditional fashion trends for something more unique but ultimately, timeless.
10. Anna Karenina: The dramatic Anna Karenina in Tolstoy's epic novel by the same name is a complex character who is both selfish and self-effacing, passionate and distant. From her earliest introduction in the novel, Anna is viewed as the thoroughly fashionable visitor from St. Petersburg. Kitty, Dolly and the other female characters marvel at her stately beauty and rich clothes, which she wears throughout the book despite her tragic life as a recluse and an embarrassment to Russian society. Anna Karenina has been adapted for film numerous times, starring actresses like Vivien Leigh, Greta Garbo and Jacqueline Bisset.