The Coolest Single Women Ever to Take Manhattan

This year marks the 50-year anniversary of Sex and The Single Girl, Helen Gurley Brown's original guide to rocking a sexy, satisfying single life. This iconic book inspired a movie, and ever since, the single-chick-hits-New York story has been done about … oh, a million times. And as far as we're concerned, it never gets old. Check out some of our favorite kickass characters.

By Amary Wiggin

Helen Gurley Brown






You Know Her From...Cosmo (1965-Present)

She wrote the manual on how young women should rock their sex appeal and financial independence in Sex & The Single Girl, and went on to edit Cosmopolitan, of course.









Ann Marie






You know her from...That Girl (1966-1971)

In this 60's sitcom, a wide-eyed aspiring actress moves to the Big Apple - and makes scraping by seem glamorous.










Tess McGill







You know her from...Working Girl (1988)

Melanie Griffith owns the 80's power suit and super-sized hair in this Oscar-winning flick about a working-class 20something who takes charge on Wall Street.
Related: The Fierce New Secret To Success








Felicity Porter






You know her from...Felicity (1998-2002)

In a spontaneous move, Felicity ditches pre-med at Stanford for college in New York to follow her high school crush. She experiences love, life, and fallout from the worst hair decision ever.









Carrie Bradshaw






You know her from...Sex & The City (1998-2004)

A shoe addict living the dream: designer duds and a one-bedroom in Manhattan, all on a writer's salary. Watching her, we can't help but wonder … how??










Andrea Sachs



You know her from...The Devil Wears Prada (2006)

Her hellish job working for a bitchy fashion editor at a New York glossy rings all too true for entry-level recent grads everywhere.
Related: How To Impress Your New Boss







Betty Suarez




You know her from...Ugly Betty(2006-2010)

As a style-challenged assistant at Mode magazine, Betty brings her own brand of awesome to the cutthroat fashion industry.








Peggy Olson







You know her from...Mad Men (2007-Present)

The deck is stacked against her, a female copywriter at a Manhattan advertisy agency in the chauvinistic 1960s. But Peggy will stop at nothing to succeed.









Karen Cartwright






You know her from...Smash (2012-Present)

She's a young out-of-towner trying to make it on Broadway in this brand-new NBC series. It's too early to know if she can bounce back from being passed over for a starring role … but we're rooting for her!









Annie Hall






You know her from...Annie Hall (1977)

In this Woody Allen romance, Wisconsin-born Annie hits the city hoping to make it as an actress and singer. Her quirky, menswear-inspired style became forever associated with 1970s New York City women.










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