The Poor Little Rich Girl's Tragic-Cool Style

Archetypes may be unrealistic, but man are they a good source of style inspiration. The Cool Girl. The Witchy Woman. The Bushwick Loft Party Attendee. The Writer Who Never Blow-Dries Her Hair. (Just me?) The best archetypes embody some sort of dissonance — i.e., they're not just stereotypes; they're a little bit more complex.

For me, the Poor Little Rich Girl will always be one of the most fascinating archetypes out there, because of its deep sense of irony. As Britney Spears once sang in "Lucky," — the greatest portrait of the Poor Little Rich Girl ever — "If there's nothing missing in her life, then why do these tears come at night?" She "has it all," and in having it all, she has nothing. It's poetry, right?

The phrase "poor little rich girl" was coined in 1913 by a playwright named Eleanor Gates, and it became a popular catchphrase when the play was made into a 1917 movie of the same name, starring Mary Pickford. You can probably guess at the plot of Poor Little Rich Girl, because it shaped the archetype as we know it today: A girl who has everything is ignored by her wealthy parents, and so, to escape her hollow existence, she hangs out with people who are more interesting than her vapid family — in other words, people who have less money.

The ultimate real-life Poor Little Rich Girl came along a few decades later. Her name was Barbara Hutton, and she fit the archetype to a T. As the heiress of the Woolworth fortune, her 1930 debutante ball was so lavish — and so poorly-timed, coming in the middle of the Great Depression — that Hutton was flown off to Europe to escape the outraged press. Financially, she had it all. Personally, her life was a wreck. Her mother died when Hutton was 5, and her father was a philandering absentee. She had seven mostly unhappy, abusive marriages, and ended up blowing through the family fortune.

Hutton may have been richer than Midas, but the most alluring Poor Little Rich Girl of the past century has to be Edie Sedgwick of Andy Warhol's Factory. Like Hutton, she was wealthy, gorgeous, troubled, and bad with her family's money; Warhol even put her in a film called Poor Little Rich Girl. She chopped her hair off, wore super-short dresses, hung out with weirdos, and died of a overdose at 28.

It's a sad archetype, but it's totally compelling, and today there's an entire entertainment economy built around it (see: Gossip Girl, Kelly Taylor of Beverly Hills, 90210, Paris Hilton). We might not want the Poor Little Rich Girl's fate for ourselves, but we definitely wouldn't mind her expensive clothes — and the ability to wear them casually, like we've got a million more in our skeleton-filled closet.

Here's how she does it:

1. Dress like it's Daddy's money

The Poor Little Rich Girl doesn't care how much her ball gown cost. She doesn't even know how much it cost. Chanel? Thrift store? Something in between? Who cares? She'll toss on whatever frothy creation is within arm's reach (and she'll look amazing in it, because — spoiler alert — it was Chanel).

2. Wear big, cheap-looking jewels that aren't actually cheap at all

Poor girls fake rich. Poor little rich girls fake poor. Something about the grass being greener?

3. Be chill about the fact that you're wearing a massive fur

The Poor Little Rich Girl is certainly not intimidated by something that required a thousand muskrat tails to create.

4. Ignore all attempts to entertain you

Her puffed sleeves look better when she's bored.

5. Wave away all fancy foods

Do you think she fits in her diamond-encrusted dress by eating caviar every day?

6. When you're not at a debutante ball, dress like you're about to cause trouble

This is her "I climbed out of the the window in priceless Dior and then changed into this" look.

7. You're allowed to look a little bonkers

Money does crazy things to people! CRAZY THINGS! CRAZY THINGS!

8. But your hair always has to look perfect. Sorry

Rich hair is made of money.

9. Accessorize with dollar bills

She could wear a $10,000 necklace (so passé), but she'd rather wear $10,000 actual dollars.

10. When you're forced to wear cheap clothes, wear pink

Pink is what normal people wear. Right?!

11. Always have a getaway outfit

Daddy is so cruel sometimes. Sometimes a girl just has to leave.

12. Your go-to makeup look should be one of discontent and deep inner sorrow

She never fails to get the flick of ennui-liner just right.

13. Dress for a side career that Daddy doesn't approve of

When the Duke of Lexington spotted her singing at the Green Mill, there was hell to pay, but she wouldn't trade her one night of freedom for a thousand white-tie affairs.

14. Always pair an off-the-shoulder gown with a bad attitude

A furrowed brow really shows off her clavicle.

15. The best accessory is a golden mirror that reflects the inescapable shallowness of your isolated life

She stares into it every night, waiting for the stock market to crash.

Images: The Weinstein Company/MGM; Tumblr (13); Gifsoup; Photobucket; Comediva