Gillian Anderson as Lily Bart in 2000’s The House of Mirth
This aging society girl was always a vision in beautiful dresses and jewels. But because she wasn’t as wealthy as her friends, she was always running up dress-maker debt.
Edith Wharton writes: “The remaining dresses, though they had lost their freshness, still kept the long unerring lines, the sweep and amplitude of the great artist’s stroke, and as she spread them out on the bed the scenes in which they had been worn rose vividly before her. An association lurked in every fold: each fall of lace and gleam of embroidery was like a letter in the record of her past.”
Dorian Gray, The Picture of Dorian Gray
Ben Barnes as the title character in Dorian Gray (2009)
This fin-de-siècle dandy hides a dark secret: While his face stays young and beautiful, a hidden portrait shows his true, festering and debauched, soul.
Oscar Wilde writes: “That evening, at eight-thirty, exquisitely dressed, and wearing a large button-hole of Parma violets, Dorian Gray was ushered into Lady Narborough’s drawing-room by bowing servants.”
Holly Golightly, Breakfast at Tiffany’s
Audrey Hepburn in Breakfast at Tiffany’s (1961)
Like Lily Bart decades earlier, Holly Golightly is a New York socialite who seemed to appear out of nowhere, shrouded in glamorous mythology.
Truman Capote writes: “She was still on the stairs, now she reached the landing, and the ragbag colors of her boy’s hair, tawny streaks, strands of albino blond and yellow caught the hall light. It was a warm evening, nearly summer, and she wore a slim, cool black dress, black sandals, a pearl choker. For all her chic thinness, she had an almost breakfast-cereal air of health, a soap and lemon cleanness, a rough pink darkening in the cheeks. Her mouth was large, her nose upturned. A pair of dark glasses blotted out her eyes. It was a face beyond childhood, yet this side of belonging to a woman. I thought her anywhere between sixteen and thirty; as it turned out, she was shy two months of her nineteenth birthday.”
Tilda Swinton in 1992’s Orlando
A mysterious figure who lives for centuries and changes sexes midway through, Orlando is the original androgynous fashion icon.
Virginia Woolf writes: “Orlando had now washed, and dressed herself in those Turkish coats and trousers which can be worn indifferently by either sex.”
Scarlett O’Hara, Gone with the Wind
Vivien Leigh in 1939 as Scarlett O’Hara
The first thing we learn in Gone with the Wind is that Scarlett isn’t beautiful. But this Civil War-era firebrand made up for it by dressing well, in high southern belle style.
Margaret Mitchell writes: “Her new green flowered-muslin dress spread its twelve yards of billowing material over her hoops and exactly matched the flat-heeled green morocco slippers her father had recently brought her from Atlanta. The dress set off to perfection the seventeen-inch waist, the smallest in three counties, and the tightly fitting basque showed breasts well matured for her sixteen years.”
Jay Gatsby, The Great Gatsby
Robert Redford as Jay Gatsby in The Great Gatsby (1974)
Wealthy and successful Jay Gatsby is all about personal myth-making — and that means investing in beautiful, expensive, Jazz Age clothing.
F. Scott Fitzgerald writes: “An hour later, the front door opened nervously, and Gatsby, in a white flannel suit, silver shirt, and gold-colored tie hurried in.”
Emma Bovary, Madame Bovary
Isabelle Huppert in Claude Chabrol’s Madame Bovary (1991)
Emma’s addiction to beautiful things may have been her downfall (perhaps even more than her famous adultery), but she sure did look nice wearing them!
Gustave Flaubert writes: “She would come directly, charming, agitated, looking back at the glances that followed her, wearing her flounced gown with gold eyeglass, her dainty shoes, all sorts of elegant trifles that he had never enjoyed, and exhaling the ineffable seduction of yielding virtue.”
Rupert Psmith, the novels of P.G. Wodehouse
A recurring character in Wodehouse’s books, Psmith is a quick-tongued dandy who’s been expelled from Eton.
P.G. Wodehouse writes (in Mike and Psmith): “A very long, thin youth, with a solid face and immaculate clothes, was leaning against the mantelpiece. As Mike entered, he fumbled in his top left waistcoat pocket, produced an eyeglass attached to a cord, and fixed it in his right eye.”
Lady Brett Ashley, The Sun Also Rises
Ava Gardner in The Sun Also Rises (1957)
Brett is the trend-setting It Girl of ’20s Europe, winning the hearts of every man she meets, despite the fact that she’s engaged.
Ernest Hemingway writes: “Brett was damned good-looking. She wore a slipover jersey sweater and a tweed skirt, and her hair was brushed back like a boy’s. She started all that. She was built with curves like the hull of a roaring yacht, and you missed none of it with that wool jersey.”
Darling Daintyfoot, Our Lady of the Flowers
As the beloved pimp who lived with a drag queen named Divine, Jean Genet’s Darling Daintyfoot was a pioneer of contemporary hustler fashion.
Jean Genet writes: “Darling has gradually exchanged his clothes, which were shabby from months in a cell, for some elegant worsted suits and scented linen. The transformation has delighted him.”