Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
WeirdNew York’s Most Fashionable Characters
By Tyler Coates
@tylercoates
Published
Sep. 13, 2015, 9:00 a.m. ET
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Everett Collection
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20. Chelsea Brown (Rosario Dawson), Top Five
This New York Times reporter keeps her easy, breezy style on the surface, which covers up an inner life that's a little more complex. Plus, that undercut! Damn, girl.
[Where to stream Top Five]
This New York Times reporter keeps her easy, breezy style on the surface, which covers up an inner life that's a little more complex. Plus, that undercut! Damn, girl.
[Where to stream Top Five]
Photo: Paramount Pictures; Courtesy Everett Collection
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19. Mary (Parker Posey), Party Girl
Bored librarian by day, club-hopping scenester by night. Parker Posey's breakthrough role saw her character nailing a day-to-evening look with surprising aplomb.
[Where to stream Party Girl]
Bored librarian by day, club-hopping scenester by night. Parker Posey's breakthrough role saw her character nailing a day-to-evening look with surprising aplomb.
[Where to stream Party Girl]
Photo: First Look Pictures; Courtesy Everett Collection
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18. Newland Archer (Daniel Day-Lewis), The Age of Innocence
How else to bring a dashing masculinity to the Gilded Age without trenchcoats, fancy hats, high collars, and that rugged upper-class charm?
[Where to stream The Age of Innocence]
How else to bring a dashing masculinity to the Gilded Age without trenchcoats, fancy hats, high collars, and that rugged upper-class charm?
[Where to stream The Age of Innocence]
Photo: Columbia Pictures; Courtesy Everett Collection
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17. Bill Cunningham, Bill Cunningham New York
He doesn't just document the cutting edge fashion in the bustling metropolis of Manhattan — the Vogue photographer has a signature look all his own with his trademark blue jacket and bike, which takes him up and down the island.
[Where to stream Bill Cunningham New York]
He doesn't just document the cutting edge fashion in the bustling metropolis of Manhattan — the Vogue photographer has a signature look all his own with his trademark blue jacket and bike, which takes him up and down the island.
[Where to stream Bill Cunningham New York]
Photo: Zeitgeist Films; Courtesy Everett Collection
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16. Patrick Bateman (Christian Bale), American Psycho
Sure, his suits never really manage the industrial equipment he uses to enact his psychopathic fantasies, but Bateman definitely looks the part at Cipriani.
[Where to stream American Psycho]
Sure, his suits never really manage the industrial equipment he uses to enact his psychopathic fantasies, but Bateman definitely looks the part at Cipriani.
[Where to stream American Psycho]
Photo: Lionsgate; Courtesy Everett Collection
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15. Susan Thomas (Madonna), Desperately Seeking Susan
Featuring the pop star's signature early '80s looks, this character defined an era of '80s fashion that embraced messiness and cluttered accessories.
[Where to stream Desperately Seeking Susan]
Featuring the pop star's signature early '80s looks, this character defined an era of '80s fashion that embraced messiness and cluttered accessories.
[Where to stream Desperately Seeking Susan]
Photo courtesy Everett Collection
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14. Tina (Rosie Perez), Do the Right Thing
It's the hottest day of the summer, but that doesn't mean you can't still look your best in a sexy and revealing look on the busy streets of Bed-Stuy!
[Where to stream Do the Right Thing]
It's the hottest day of the summer, but that doesn't mean you can't still look your best in a sexy and revealing look on the busy streets of Bed-Stuy!
[Where to stream Do the Right Thing]
Photo courtesy Everett Collection
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13. Joe Buck (Jon Voight), Midnight Cowboy
Long before Urban Cowboy made the term popular, Jon Voight's naive young hustler rocked the wild west look while roaming the streets of Manhattan in this controversial, Oscar-winning film.
[Where to stream Midnight Cowboy]
Long before Urban Cowboy made the term popular, Jon Voight's naive young hustler rocked the wild west look while roaming the streets of Manhattan in this controversial, Oscar-winning film.
[Where to stream Midnight Cowboy]
Photo courtesy Everett Collection
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12. Tess McGill (Melanie Griffith), Working Girl
Staten Island native Tess ditches the stone-washed denim and big, crispy hair for a softer and professional look as she rises in the ranks of a Wall Street firm, bringing an outsider's spin on the working-girl look.
[Where to stream Working Girl]
Staten Island native Tess ditches the stone-washed denim and big, crispy hair for a softer and professional look as she rises in the ranks of a Wall Street firm, bringing an outsider's spin on the working-girl look.
[Where to stream Working Girl]
Photo: 20th Century Fox; Courtesy Everett Collection
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11. Priest (Ron O’Neal), Super Fly
Nowadays, coke dealers don't possess the unabashed style they did back in the '70s.
[Where to stream Super Fly]
Nowadays, coke dealers don't possess the unabashed style they did back in the '70s.
[Where to stream Super Fly]
Photo courtesy Everett Collection
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10. Little Edie Beale, Grey Gardens
A former Manhattan socialite (and a cousin to Jacqueline Kennedy), Edie Beale lived with her mother in their dilapidated East Hampton mansion. Most importantly, she curated a look she identified as her "revolutionary costume."
[Where to stream Grey Gardens]
A former Manhattan socialite (and a cousin to Jacqueline Kennedy), Edie Beale lived with her mother in their dilapidated East Hampton mansion. Most importantly, she curated a look she identified as her "revolutionary costume."
[Where to stream Grey Gardens]
Photo courtesy Everett Collection
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9. Daisy Buchanan (Mia Farrow), The Great Gatsby
Though she spends most of her time on Long Island (other than an ill-fated venture into Manhattan), the quintessential flapper nailed the look of the roaring '20s with pearls, lace, and debauchery for days.
[Where to stream The Great Gatsby]
Though she spends most of her time on Long Island (other than an ill-fated venture into Manhattan), the quintessential flapper nailed the look of the roaring '20s with pearls, lace, and debauchery for days.
[Where to stream The Great Gatsby]
Photo courtesy Everett Collection
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8. Iris Steensma (Jodie Foster), Taxi Driver
I feel like girls in Bushwick are currently rocking Foster's hip teenage prostitute look even today!
[Where to stream Taxi Driver]
I feel like girls in Bushwick are currently rocking Foster's hip teenage prostitute look even today!
[Where to stream Taxi Driver]
Photo courtesy Everett Collection
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7. Annie Hall (Diane Keaton), Annie Hall
Diane Keaton plays the definitive Skiksa goddess, adding a feminine spin on menswear that became an iconic look in Woody Allen's romantic comedy.
[Where to stream Annie Hall]
Diane Keaton plays the definitive Skiksa goddess, adding a feminine spin on menswear that became an iconic look in Woody Allen's romantic comedy.
[Where to stream Annie Hall]
Photo courtesy Everett Collection
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6. Carrie Bradshaw (Sarah Jessica Parker), Sex and the City
Sure, some of those outfits were downright INSANE, but Carrie's wardrobe on the HBO series' six seasons (and two movies) was definitely iconic.
[Where to stream Sex and the City]
Sure, some of those outfits were downright INSANE, but Carrie's wardrobe on the HBO series' six seasons (and two movies) was definitely iconic.
[Where to stream Sex and the City]
Photo: HBO; Courtesy Everett Collection
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5. John Shaft (Richard Roundtree), Shaft
Steve McQueen might get credit as playing the most stylish cop in Bullitt, but Roundtree's John Shaft gives him a run for his money as his East Coast peer, rocking those turtlenecks and leather jackets with a lot of style and gusto.
[Where to stream Shaft ]
Steve McQueen might get credit as playing the most stylish cop in Bullitt, but Roundtree's John Shaft gives him a run for his money as his East Coast peer, rocking those turtlenecks and leather jackets with a lot of style and gusto.
[Where to stream Shaft ]
Photo courtesy Everett Collection
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4. Royal, Etheline, Chas, Margot, and Richie Tenenbaum (Gene Hackman, Anjelica Huston, Ben Stiller, Gwyneth Paltrow, and Luke Wilson), The Royal Tenenbaums
They might be dysfunctional as hell, but you can't say this band of brilliant, neurotic New Yorkers aren't some of the most fashionable clans in movie history.
[Where to stream The Royal Tenenbaums]
They might be dysfunctional as hell, but you can't say this band of brilliant, neurotic New Yorkers aren't some of the most fashionable clans in movie history.
[Where to stream The Royal Tenenbaums]
Photo courtesy Everett Collection
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3. Denise Huxtable (Lisa Bonet), The Cosby Show
I think it's time to shift our focus from the uncomfortable aspects of the classic NBC sitcom and its tarnished star and celebrate the gorgeous and fashion-forward Hutxtable kid who kept pushing the boundaries of style throughout the series.
[Where to stream The Cosby Show]
I think it's time to shift our focus from the uncomfortable aspects of the classic NBC sitcom and its tarnished star and celebrate the gorgeous and fashion-forward Hutxtable kid who kept pushing the boundaries of style throughout the series.
[Where to stream The Cosby Show]
Photo: NBC; Courtesy Everett Collection
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2. Miranda Priestly (Meryl Streep), The Devil Wears Prada
Inspired by Vogue editor Anna Wintour, the fiendish Miranda Priestly certainly wouldn't be a friend to call upon in need — that is unless you were having a fashion emergency.
[Where to stream The Devil Wears Prada]
Inspired by Vogue editor Anna Wintour, the fiendish Miranda Priestly certainly wouldn't be a friend to call upon in need — that is unless you were having a fashion emergency.
[Where to stream The Devil Wears Prada]
Photo: 20th Century Fox; Courtesy Everett Collection
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1. Holly Golightly (Audrey Hepburn), Breakfast at Tiffany’s
Holly Golightly is pretty much the ideal New York woman — women want to be her, men want to be with her. Sure, there's a certain fragility under the surface, but Holly distracts and covers up her flaws with borrowed jewels and Givenchy frocks.
[Where to stream Breakfast at Tiffany’s]
Holly Golightly is pretty much the ideal New York woman — women want to be her, men want to be with her. Sure, there's a certain fragility under the surface, but Holly distracts and covers up her flaws with borrowed jewels and Givenchy frocks.
[Where to stream Breakfast at Tiffany’s]
Photo: 20th Century Fox; Courtesy Everett Collection
